What’s missing from most of the guidance on having hard conversations is a question that should come first: can everyone in this conversation participate effectively in it?

That sounds like an obvious thing to check, right? It often isn’t. Most managers think about logistics (when, where, who) and content (what they’re going to say, how they’re going to say it) without thinking intentionally about whether the format, the environment, or the setup creates barriers for other participants.

This issue is a practical checklist for building accessibility into hard conversations before they start, whether they’re happening in person, virtually, or some mix of both.

Workplace accessibility isn’t just good practice: in your locality it may be a legal requirement. The Americans with Disabilities Act (ADA) in the United States, the Equality Act in the United Kingdom, the European Accessibility Act across the EU, and the Accessible Canada Act are all examples of legislation that sets a baseline for ensuring employees with disabilities can participate equally in workplace meetings and communications. Wherever you’re reading this, it’s worth checking what applies in your context.

⭐ One last thing before we get into the checklist, one principle that is my personal starting point: the person you’re meeting with is the expert on their own needs.

People with disabilities and neurodivergent individuals are best positioned to identify what works for them, and those needs vary significantly from person to person even when people share facets of the same identity or diagnosis. A checklist gives you good defaults and a starting point. It doesn’t replace asking. The most important accessibility practice a manager can have is genuine curiosity and the habit of asking directly, early, and without assumption: “Is there anything I can do to make this conversation easier for you to participate in?” Then listen, take it seriously, and follow through. Everything else in this checklist is secondary to that practice.

3 Common Gaps

These are all fixable with some intentional thought and action ahead of the meeting:

• Poor audio or video in hybrid settings 🚩

  When someone is joining remotely while others are in the room, the in-room audio almost always sounds worse than it should. The remote participant hears a wall of ambient noise, can’t tell who is speaking, and misses things. This matters in any meeting. In a hard conversation, it can be a serious liability.

• No captions 🚩

  Auto-captions on many platforms are gaining accuracy and take about 30 seconds to enable. Real-time professional captioning (called CART, or Communication Access Realtime Translation) is more accurate and worth the cost for high-stakes conversations. Not having captions at all is a gap that excludes people who are deaf or hard of hearing, people who process written language more effectively than spoken language, and anyone in a noisy environment.

• Not identifying who is speaking 🚩

  When participants don’t say their name before they speak, low-vision participants, participants using screen readers, and people reviewing transcripts or recordings afterward lose critical context. It’s a small norm to establish and a big barrier to remove.

Before the meeting: what to send and set up

For any hard conversation, in person or virtual:

• Include an accommodation request statement in the meeting invitation. One sentence and a link or contact is enough: “If you need any accommodations to participate fully in this meeting, please let me know by [date] so I can arrange support.” Ask before, not after.

• Share any supporting materials (agenda, talking points, documents) in advance whenever possible. If you’re sharing files, use formats that screen readers can access (Word documents or HTML, not image-based PDFs).

• If you’re using a presentation or slides, send the file directly rather than sharing your screen. Screen reader software can’t interact with shared screens in most platforms.

For virtual or hybrid conversations specifically:

• Enable closed captions and transcripts before the meeting starts, not during it.

• If the conversation is high-stakes and accuracy matters, consider CART (professional live captioning) rather than relying on auto-generated captions.

• If you’re including a sign language interpreter, confirm their video will be visible and pinned throughout the call (including in any recording you share afterward).

• Test your audio setup before the meeting. This matters more in hybrid settings, where in-room microphones impact the experience of remote participants. If you’re joining from a conference room, check that the microphone picks up everyone in the room clearly.

• Have a phone dial-in option available as a backup, in case someone’s video connection fails or isn’t accessible for them.

For in-person conversations specifically:

• Send participants venue accessibility information in advance. This should include: the accessible entrance and travel path from parking or transit, whether there are stairs or an elevator, the nearest parking with accessible spaces, step-free access to the meeting room, the location of an accessible restroom, whether the building has a quiet or low-sensory area available if needed, and a note about the security checkpoint process if one exists. Sending this in advance removes the burden of asking on arrival.

During the meeting

• Open with a brief visual description of yourself if this is a virtual meeting where participants may not know you by video. For example: “I’m [name]. I’m joining from my office in XYZ building, sitting at a desk in front of a bookshelf.” This is particularly helpful for participants with low vision.

• State the agenda at the top of the conversation, even in a one-on-one.

• Ask all participants to say their name before speaking, and model it yourself. It sounds a little formal the first time but becomes natural quickly and makes a real difference for anyone relying on transcripts or captioning.

• Describe any visual information you reference. If you share a document or gesture toward something on screen, say what it is rather than pointing to it.

• Use platform features like polling or non-verbal reactions rather than the chat when you want to invite participation. Chat messages interrupt screen reader users by being read aloud mid-conversation. If chat is active, designate someone to read relevant messages aloud so they’re part of the conversation for everyone.

• Share the recording and/or transcript with all participants afterward, if recording is allowed.

Building accessibility in by default doesn’t require a long checklist every time. Most of it becomes habit after a few repetitions. What it does require is the decision to slow down before the conversation instead of treating logistics as the part you rush through to get to the “real” work.

If this article resonates for you or you know someone who might find it useful, please share this article so more leaders can find Altitude! Thank you for being a reader, I appreciate you <3

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Additional resources (an incomplete list)

The W3C Web Accessibility Initiative publishes a comprehensive, disability-community-backed checklist for making meetings and events accessible in any format: Making Events Accessible (W3C WAI)

The Ability Center has a practical guide specifically for virtual meetings, written for managers and organizers: Accessible Virtual Meetings Guide

Section508.gov covers ADA-grounded guidance for accessible workplace meetings: Accessible Meetings (Section 508)

I’d appreciate your support at any level - free or paid - as it helps more leaders find Altitude! Thank you for being a reader and part of this community. You mean a lot to me.

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If you have additional resources on workplace accessibility to share, or an experience where accessibility has been important for your / others’ experience in the workplace, I would love to hear about it. You are welcomed and encouraged to leave a comment!

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See you next Tuesday,

Kaleigh

New to Altitude or need a quick reference guide? Here’s a charcuterie board of the Top 5 Most Useful Articles, selected just for you.

Pick something relevant to your life right now, a topic you’ve been meaning to learn more about, or something you wish your manager knew and start there.

Not sure where to start? That’s valid. What about something that feels like gossip but isn’t, really…

Most Useful Articles

This first one comes with a free PDF download of The Emotional Temperature Framework: a set of my favorite open-ended questions to start any 1:1 off on the right track (and determine whether continuing with your 1:1 agenda is really the right call, depending on someone’s emotional weather pattern).

Onward…

This next one lays out a clear path to getting promoted, at any level, period. If a promotion isn’t part of your development goals right now, it’s worth reading for general best practices on how to make sure the amazing work you (and your team(s)) are doing each day is seen / recognized in all the right ways.

This one gives you 3 questions to screenshot and re-use in every single team conversation (whether it’s your team or someone else’s) where things are a little bit (or a lot a bit) stuck and you actually want to move things forward in an effective way.

This last one on the list is not just another First 90 Days article, it’s a compilation and distillation of everything I’ve learned in each of the (now, 4 and counting) management role transitions I’ve navigated. Importantly, I built it to feel authentic to me as someone whose default setting is building relationships first. Spoiler alert: I’m using this exact framework right now for a role transition - feel free to reach out and ask me how that’s going!

Finally, below is a link to The Manager’s Conversation Toolkit. Inside the Toolkit you’ll find four ready-to-deploy 1-on-1 conversation templates for the situations that are hardest to walk into without a plan: career development, performance discussions, navigating change and ambiguity, and rebuilding trust. There’s also a bonus framework included: for what to actually say when someone on your team is struggling or in crisis (including what not to say, which is definitely the tougher list).

A note on subscriptions: Altitude is a paid newsletter with a free tier. The free issues like those you see above are real content, not teasers. But the paid tier goes further and whenever upgrading makes sense for you, it’s available.

If your company has a learning & development reimbursement program, it’s worth checking into to see if leadership development resources like this are eligible for reimbursement (and submitting your subscription receipt if so!)

I’m curious: which article(s) in this list did resonate with you? Is there another you’d recommend adding? A topic you’d recommend be added to the Altitude article “backlog”?

Please feel free to add a comment below! I read every one :)

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Talk soon - a new Altitude article arrives each Tuesday, so I’ll see you then!

Kaleigh

I fell into the warmth trap for years before I understood what it was costing me.

I say this as someone who does lead with warmth, who has “one of those faces” people feel comfortable telling hard things to, and who took being described as “a pleasure to teach in class” as a kid a little too seriously. So I know what the trap looks like from the inside.

I know this because I did it. I would tell people directly, “I’m working on being more direct and clear when I give feedback,” then soften my feedback anyway and wonder why nothing changed. The irony is that no one pushed back on my style because what they were receiving was warm, supportive Kaleigh, and who’s going to complain about that? I was getting away with it. And my team was leaving conversations unclear on what had happened, what I actually thought, and what they were supposed to do differently.

That’s not kindness. That’s abdication dressed up as warmth.

Maybe you recognize this too…or know someone who falls into this same trap.

If this article resonates for you or you know someone who might find it useful, please share this article so more leaders can find Altitude! Thank you for being a reader, I appreciate you <3

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What The Warmth Trap Looks Like

You’re sitting across from someone who has done something that needs to be addressed. Maybe they handled a meeting badly. Maybe their behavior missed a norm. Maybe the feedback they’ve been getting hasn’t landed and it’s time for a direct conversation.

You care about this person. You don’t want to damage the relationship. You don’t want them to feel bad. So your instinct (often unconscious, often well-practiced since childhood if you grew up as the peacemaker in your family) is to smooth, to soften, to de-escalate.

It might sound like this: “I’m sure you were just confused about what we were trying to achieve that meeting, which is totally okay!”

Or: “Honestly, I think this is on me. I wasn’t communicating clearly enough and next time I’ll make sure I’m setting you up better.”

Both of those sentences feel generous. They protect the other person from discomfort. They keep the relationship warm.

Here’s what they also do: they leave no room for the other person to reflect, to share their actual experience, to take any accountability, or to understand what actually needs to change. The person walks out of the conversation feeling fine. Maybe a little confused. But fine.

And nothing changes, because nothing actionable was discussed.

The Research on Warmth and Competence (And Why We Need Both)

There’s research that helps explain why this matters: social psychologist Amy Cuddy and her colleagues have shown that people judge others on two dimensions almost instantly: warmth and competence.

• Warmth tells them about your intentions.

• Competence tells them whether you can deliver on those intentions.

You need both.

The warmth trap is what happens when warmth crowds out competence. Not because clear feedback is cold (it isn’t) but because the avoidance of clarity signals, at some level, that you can’t or won’t do the hard thing. People may not consciously register this. But they feel it. And over time, it erodes their confidence in you as a leader, even as they keep liking you.

Being liked is not the same as being trusted. Being warm is not the same as being effective. And the leader who is warm without being clear is often, quietly, not being taken seriously.

Life Outside The Trap

Getting out of the trap, for me, meant learning to hold the discomfort instead of resolving it prematurely. To ask questions rather than fill in the narrative for the other person. To say what I actually observed, without the softening layer that made it about my uncertainty instead of their behavior.

The clear version of the conversation I described above might sound like: “I want to talk about what happened in that meeting. Can you walk me through how you were thinking about it?” And then stop talking. Let them respond. Let there be silence if there needs to be silence. Let the conversation go somewhere real.

Warm and clear are not opposites. You can be genuinely kind and genuinely direct at the same time. In fact, the clearest gift you can give someone who is falling short is an honest conversation about it, held with care. That is both warm and competent. That is what people actually need from a leader.

The goal isn’t to stop being warm. It’s to stop letting warmth be a reason to say less than you mean.

I’d appreciate your support at any level - free or paid - as it helps more leaders find Altitude! Thank you for being a reader and part of this community. You mean a lot to me.

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How do you balance warmth and clarity when providing feedback? I’d love to hear from you in the comments!

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See you next Tuesday,

Kaleigh

Hard conversations, ugh. Most managers have anxiety and avoid them because nobody taught them how to have these conversations, not because they don’t care or don’t want to help.

Technical training exists. Process training exists. There are certifications for project management and cybersecurity and agentic AI and just about everything. But “how to sit across from someone you care about and tell them something hard”? That is largely self-taught based on the situation and can feel reactive rather than proactive.

Like a lot of leaders, I learned the hard way. From conversations that went sideways. From feedback I gave too late, too vaguely, or with too many secondhand observations in the mix.

From the time a stakeholder expressed disappointment to me in a meeting and I went back to my direct report with more directness than I’d ever used with her (more out of exhaustion than intention) - only realizing later that being crystal clear with what I needed had actually worked.

Below is the framework for hard conversations I’ve built from all of that hard won experience. It applies across the full range of hard conversations: performance, trust, navigating change, and supporting someone in distress. The structure is the same every time, but you can customize this structure to situations across these categories.

Before the conversation

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Here’s something nobody tells you when you become a manager / leader: your team doesn’t need another person doing the work.

They need two things that sound like opposites, but aren’t.

🛡️ They need you to be the shield — the person who stands between them and the distractions that would break their focus on their priorities.

🪜 They need you to be the ladder — the person who carries their work into rooms they aren’t and makes sure it is acknowledged and celebrated.

These two jobs together are some of the most underrated and highest-leverage work a leader does. They don’t show up in a job description. Nobody includes “shield and ladder” in a performance review. But the teams that feel most protected and most motivated are almost always led by someone who figured this out.

Here’s how both work in practice.

The shield 🛡️

There’s a common version of management where your job is to field every request that comes in, pass those requests down to your team, and measure success by how quickly things get done. This model treats your team like a factory: work arrives, gets processed, comes back out.

The problem is that this isn’t how complex technical or creative work actually works.

Constant context-switching is one of the fastest ways to destroy momentum, and nothing creates context-switching faster than a team whose priorities change based on whoever just sent an email.

The manager’s job is to hold the priorities. And to be the buffer when something tries to change them without good reason.

For my team, this looked like a system with a simple structure: we had clear priorities that we reviewed on a regular cadence (in 1:1s, as a team during our regular meetings). The intent was that everyone had clarity on what they were working on when and why it was the priority.

When a new request came in from a stakeholder, the team member had a choice: forward it to me for triage (so they could stay focused on current work), or bring it to me for a quick check-in before agreeing to any change in direction. Either way, the decision was conscious and clear, not just absorbing another “emergency request” because someone asked.

The effect was that most requests got answered, most priorities stayed stable, and the team wasn’t in a constant state of reactive scramble. They knew I was watching the incoming requests. Their job was to stay focused on the work.

Being the shield doesn’t mean saying no to everything. It means being the one who decides, strategically with your team, what gets through the filter and what can wait.

The ladder 🪜

The other side of this is what happens when we make progress visible upward.

Your team is doing excellent work. The question is whether anyone above you knows it. And the honest answer, for a lot of teams, is no — not because the work isn’t good but because visibility and advocacy take intentional effort.

Technical people do the work. Managers go to the stakeholder meetings. The connection between those two things doesn’t happen automatically.

The ladder is that connection. Your job is to be in the rooms your team isn’t in and make sure that their names, their accomplishments, and the specific positive impact of their work get said out loud in those rooms.

I started doing this systematically by publishing a weekly accomplishment summary for my engineering team. Every week I published a short data-backed summary of what we completed and the positive impact for the projects we supported. I sent it to the team directly (so they could get an instant dopamine hit!) and copied our organization’s director and the directors of the project teams our work had benefited that week.

The directors often responded. “Great job, thank you” on a email thread sounds like a small thing, but for a team that had been heads-down on gnarly work for months (even years) without much visibility into how it was landing, it wasn’t small.

It told them someone at that higher level knew their names and knew what they’d built. And it was consistent praise and validation, not just when someone did something extraordinary, but every single week.

That’s the ladder. You carry the work up. The visibility comes back down. Your team feels seen by the people with the power to reward them because they actually are seen and valued.

New managers tend to think of the bulk of their job as managing down: supporting the team, unblocking the work, setting priorities. That’s real and it’s important.

But some of the highest-leverage work you do runs in the other two directions: protecting focus below you by shielding laterally and making work visible above you.

The shield and the ladder. You’re both at the same time.

I’d love to hear your versions of these. What does protecting your team’s priorities look like for you? How do you carry their work upward? Leave a comment, send a note, or find me on Substack Notes. I read every comment and restack Note and I reply to them as well 🫶🏻

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I’d appreciate your support at any level - free or paid - as it helps more leaders find Altitude! Thank you for being a reader and part of this community. You mean a lot to me.

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See you next Tuesday,

Kaleigh

I feel like most “First 90 Days” content is written for leaders who had time to plan for the transition.

If you’re reading Altitude, there’s a good chance you didn’t get the luxury of planning. You were excellent at your job and someone put “Manager” in your title or made you a technical leader in some capacity and here you are trying to figure out what you’re actually supposed to be doing as the actual work stacks up.

This resource is specifically for you. Not a generic onboarding checklist from a business book; a specific list of things that made a difference in my management / leadership journey and that I’ve seen matter for the leaders I’ve coached since. The commentary below each item is the point since a checklist without context is just a to-do list.

☐ Meet 1:1 with every person on your team in the first two weeks

Don’t wait. Don’t do group introductions and call it done. One-on-one time with each person is the fastest way to start building individual trust and those first conversations set a tone and foundation for your relationship.

Ask four questions in each one: “What’s going well?”, “What are the challenges or roadblocks we’re running into?”, “What ideas do you have for how we could improve?”, and finally: “What’s one thing I could do to better support you and the team?”

That last question will feel vulnerable to ask but I’ve gotten some of the best and most useful answers from asking it 🫶🏻

☐ Build your stakeholder map

At the end of each 1:1 ask two more questions. These two are doing a lot of quiet work: “Who else should I talk to?” and “Who relies on us for support?”

Together, they start to build your stakeholder map: a picture of who the important relationships are, who depends on your team’s work, and who your team depends on in return. You won’t have this picture on day one but it’s essential for your team’s success and your success as a leader at the center of a web of relationships that make the technical work happen effectively. These questions build it gradually, from the people who actually know. 🕸️

☐ Ask your manager to collaborate with you to define what success looks like at 30, 60, and 90 days

This is the ask new leaders are most reluctant to make, usually because they don’t want to seem like they don’t already know the answer. I recommend it since it’s a huge trust building opportunity and establishes a collaborative partnership paradigm between you and your manager 🤝

“I’d love to work with you to define two or three measurable things that would tell us both I’m on the right track at 30, 60, and 90 days” is a completely normal and valid thing to request.

Most managers are relieved when you ask it. It means you’re both looking at / agreeing upon the same target(s). It also inherently establishes check-in points where you all can talk about your progress toward those target(s).

The alternative (guessing, mind reading, assuming you know the answer) means you are increasing the risk that you and your manager are tracking entirely different definitions of success and you won’t find out until it’s causing tension and conflict later on.

Early alignment between you and your manager is a smart investment. 💸

☐ Follow up on feedback. Tell people what you heard and what you did (or plan to do) with it.

This is the most underrated item on this list.

You’re going to collect a lot of input in those early 1:1s: ideas, frustrations, suggestions, hopes. What happens next determines how much people trust you with future feedback.

If you heard something and made a decision based on it, say so. “After our conversation I decided to do X — here’s what I decided and why” is a trust-building sentence. It tells people their input has value and drives real world results. Most new managers collect feedback and go quiet. Don’t be most new managers. 🎯

☐ Tell your team and your manager how you prefer to communicate and ask how they prefer to communicate

This one might be the most skipped item on this list and in my experience it’s one of the most important.

You have preferences about how you receive feedback, information, and recognition. Your team members have preferences too.

Most of us default to the style that feels natural to us and never actually say it out loud which means at least some of those conversations are landing wrong for at least some people and nobody acknowledges it.

This applies to your manager just as much as your team. Early in my career I learned to adapt how I communicated to match how my manager actually processed information, and it changed everything about how effectively we collaborated. It’s not performing someone else’s style, it’s more like translating for your audience. Communication is only useful if it actually lands.

One question that opens the door: “Is there a way you prefer to get updates from me?” Most managers appreciate being asked.

☐ For in-person teams: create a small ritual for celebrating wins

This one sounds silly and obvious, but it’s harder than you’d think.

It’s easy to get swept up in the day to day hustle of calendars and emails and project updates without pausing to recognize the incremental progress we make each week!

For my current teams, we have a cowbell ceremony. Literal cowbells. Every Friday, we ring the cowbells for every task we completed as a team that week: big wins, small wins, all of them.

It sounds like a small thing but it created a stable, recurring moment where the teams can count on celebrating their own progress together instead of just moving on to the next thing. Not everyone attends every ceremony, but every person who attends walks away with a smile.

You don’t need a cowbell specifically, but find the version of this that works for your team and build it early. Early momentum is real, and a small weekly ritual that marks it is worth creating.

The through-line across all of these is the same thing: your first 90 days as a leader are not about proving you have all the answers. They’re about making it clear that you’re paying attention, that you’re taking the relationships you are building seriously, and that you intend to earn the trust you’ve been given rather than assume it came with the title.

That’s enough to get started 🙌🏻

The Manager’s Conversation Toolkit (pinned at the top of the paid subscriber section) includes 1:1 conversation templates built for these exact early conversations. Paid subscribers have instant access.

I’d appreciate your support at any level - free or paid - as it helps more leaders find Altitude! Thank you for being a reader and part of this community. You mean a lot to me.

Subscribe now

I’d love to hear what’s on your own first-90-days list. Is there something that made a real difference for you, or something you wish you’d known sooner? Leave a comment, send a note, or find me on Substack Notes! I read every comment and reply back.

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See you next Tuesday,

Kaleigh

Last week I walked into a manager’s office just to say hi and good morning.

No agenda. No meeting on the calendar. Just a check-in, the kind of visit that starts casual and often ends up going deeper than intended.

This manager told me, almost in passing, that she was going to miss me when I left for an upcoming role. Not just our working relationship, but me specifically because I always seemed to have the right technical context when she needed it. Without that (and without me) she was worried she’d flounder. That she’d accidentally lead her team in the wrong direction or fail to give the more inexperienced people on her team the guidance they actually needed.

I’ve been in that exact headspace before. The internal spiral of what if I’m not what this team actually needs? Not just about technical expertise, but about tenure and context and age and all of the layers that stack up when the people you’re leading have been doing this longer, know the history you haven’t lived yet, and have expertise you’re still building toward.

All three of those things were true for me too at various points, especially after role transitions. They are true for her too and probably true for you at some point in your development path.

What I told her is something I had to learn for myself the slow way, and something I now believe enough to say out loud:

The most valuable thing you can bring to a room full of people who know more than you isn’t answers, it’s questions.

The right questions, asked at the right moments, do more work than any answers you could give a team.

Here’s what I mean. The reason “asking the right questions” sounds like an obvious answer is that most of the time it’s treated like a placeholder. Vague, deferential questions that signal you want someone else to do the thinking for you don’t move teams and projects forward. What moves everyone forward is a specific, action-oriented kind of question, one our team is often too close to the work to ask themselves.

The questions I actually walked through with the manager I mentioned were:

✅ “Where does this fall in our priorities right now — and does anything need to shift?”

This is the question only a manager can really own. Your team knows what they’re working on. They often don’t know whether the relative priority of that work has changed based on things you’ve heard in other rooms. Asking explicitly, on a regular cadence and not just when something breaks, keeps priorities from going stale without anyone noticing.

✅ “What dependencies, roadblocks, or help needed do we have documented so far?”

This is the question that surfaces what’s visible and not yet visible. The team knows what they’re building. They don’t always have space to name what’s getting in the way or what they’re waiting on. Asking it explicitly, as the manager, creates that space without requiring you to know the technical answer.

✅ “What technical debt or accumulated shortcuts are we taking on here (or paying down)?”

Every significant piece of work either creates future complexity or addresses existing complexity. You don’t have to understand the specifics of that complexity (aka technical debt) to ask whether it’s being tracked. This question signals to the team you care about the long-term health of the work, not just the immediate output. That matters more than most managers realize.

When I left that manager’s office I told her the same thing I’ve told myself in every version of this situation: your job isn’t to be the smartest technical person in the room. It’s to create the conditions where the smartest technical people in the room can do their best work. That is a completely learnable, completely different skill set and it doesn’t require you to know everything first.

The fear that you’re not technically deep enough to lead effectively will probably not go away entirely. What changes, with time and practice, is your ability to recognize that the fear is telling you the wrong thing. It’s not evidence that you can’t do this. It’s evidence that you care and that’s a great starting point to take action from.

If this resonated, you might also like Issue #4, “When Your Team Knows More Than You Do”, which goes deeper on the 4 strategic shifts that changed how I lead technical experts. Paid subscribers have access in the subscriber section.

I’d appreciate your support at any level - free or paid - as it helps more leaders find Altitude! Thank you for being a reader and part of this community. You mean a lot to me.

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I’d also love to hear your version of this. The moment you realized asking the question was sometimes more valuable than having the answer. Leave a comment, send a note, or find me on Substack Notes! I read everything and reply to as many as I can.

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See you next Tuesday,

Kaleigh

If you’ve been reading since Issue #1, you might remember a question I mentioned that spiraled in my head during my first management assignment: “If I’m not a technical expert in the room, how can I be of help to this team?” During that particular time, I had a lot of complicated feelings about this question and no answers. As you’ll read below, I eventually figured out an answer and it’s way simpler than I expected:

Your job as a manager isn’t being the technical expert.

That’s all. That’s the whole thing. It seems obvious, but I’ll explain why it was tough for me to figure out.

When I transitioned into my first management assignment, I arrived to a team of engineers and techs whose experience in their technical domains was longer than I’d been an engineer…and longer than I’d been in engineering school before that. My first instinct (the wrong one, it turns out) was to work to close the knowledge gap. I started learning the details of every project within the team’s scope. I made a goal to get to a point where I could follow every conversation in every meeting. I was putting in the work but, without realizing it, I was chasing the wrong target. I was trying to rebuild credibility in a space that wasn’t mine to own anymore. While I was busy doing that, I was missing out what my team actually needed from me.

Fortunately, along the way I discovered that I had already set the right tone to lead this group of awesome, smart humans in my first week without even being conscious I did so. Months into that assignment one of the senior engineers on my team brought up a positive story in a 1:1. He told me that something I’d said very early on had made a real impact on how the team received me as their new manager. At the time, I tried (and failed) to remember what it was. Even after he told me I had zero memory of saying it. Those first weeks as a manager were a blur of learning, at speed, from every angle at the time. What I’d apparently told them was:

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Years before I became a manager, I had to make a shift in how I thought about the visibility of my achievements and who was paying attention.

Like many technical people I initially operated on the assumption that doing excellent work was all I had to do. If I kept my head down and focused on delivery, the people with power would magically notice the value of what I built and give me the external validation I felt I deserved. It was an appealing theory because it allowed me to focus on the technical skills I was rapidly building and strengthening, but it came with a strong sense of dissonance and disappointment when I didn’t receive “enough” recognition or when that recognition wasn’t from the “right” people. I felt I was doing all the right things and getting far less than I needed in return.

The cognitive shift happened after a casual encounter with a couple of senior leaders I knew vaguely at the time in a hallway. An innocent “how are things going?” led to me bursting into tears (which everyone handled gracefully, thankfully) and explaining through sobs that I was frustrated, burnt out, and feeling stuck.

They listened with warmth and compassion and I left the conversation with a couple of 1:1 sessions set up for the coming weeks with those leaders. In those conversations (and the many that followed over the coming years) a topic we returned to was the importance of making our achievements, goals, and interests visible to others at work so the value of the work is amplified through advocacy.

As a result, I started mentioning my interests in conversations with my manager/mentors, development discussions with people I was hoping to learn from, and interviews for new opportunities. I talked about the projects I successfully finished, the cool things I was working on next, and what I hoped to experience in my career. As I did this I noticed something: the more specific I got about my aspirations and what I was building toward, the more people showed up who wanted to help.

Not only my peers and my direct manager, but senior leaders (managers and individual contributors) with far more reach and context than I had. It turned out there were a lot of people who were willing to advocate, open doors, and make introductions; they just needed enough context to understand what I was working toward.

Learning from this experience was a turning point. Inviting people in (giving them the context they need to actually help you) is one of the most underrated skills that can add the biggest boost to anything you want to achieve, inside and outside of work.

By writing this I’m hopeful you’ll skip at least some of the frustration and crying in random hallways that I experienced and go straight to the “seen and shining” phase of your career, whether that’s as an individual contributor or as a leader.

Managing your manager is not a phrase people love because it sounds manipulative in a way that the concept isn’t intended to be.

Managing “up” is simply choosing to take active responsibility for the relationship(s) that shape almost everything about your experience at work.

Your growth, your ability to make decisions with confidence, your sense of whether you’re doing the right things, and the positive visibility and recognition that comes with doing all those things. This relationship is not your manager’s responsibility to own alone, it’s yours too. The earlier you take collective ownership, the faster the acceleration in your growth.

3 Strategies for Effectively Managing “Up”

1️⃣: Tell your manager what’s happening before they have to ask (also known as ‘no surprises’)

Technical professionals are often conditioned to trust that good work is self-evident. If we do excellent work, the right people will notice. Similarly if there’s a problem, I’ll escalate when I have more information. If I’m struggling, I’ll figure it out and bring the fully-formed solution, not the recommendation and proposed process.

These mindsets are rooted (to a certain extent) in good technical discipline, but actively work against you in a relationship with your manager.

Your manager can’t read your mind and they often have many projects and competing priorities to oversee. They are managing upward to their own leadership, fielding competing requests, and making decisions with incomplete information about a variety of topics simultaneously.

If you don’t tell them what’s happening in your world (the good, the bad, and the ugly) they have to guess, and there’s a high risk they may guess wrong (or not have capacity to guess at all).

🛠️ The fix: before your next 1:1, write down one thing your manager doesn’t know that they probably should. A decision you made and why. A risk on the horizon. Something you need from them that you haven’t said out loud.

Then simply make this visible to them and make it a habit. “Here’s something on my radar that I wanted to make sure you were aware of” is a sentence that will change how much your manager is able to advocate for you and offer help when you and your team need it.

This is also a positive trust-building cycle: each time your manager learns they can expect you to proactively share information so they can collaborate with you to take action based on your feedback.

2️⃣: Learn how your manager communicates and processes information

Each person (managers or individual contributor) has their own preferences on how they receive and communicate information. Some want to know the bottom line (e.g., results, outcomes, facts, etc.) first and will ask questions if they want more detail. Some want to think out loud and need space to talk through a problem before they’re ready to decide. Some prefer written context before having a conversation; others find this bureaucratic and prefer to talk first and document later.

Most of us default to communicating in a way that mirrors how we prefer to receive information. However, this presents a risk that our preferences don’t match our manager’s preferences.

🛠️ The fix: figuring out your manager’s preference isn’t complicated: you can observe them (how do they run meetings, how do they give feedback, what do they tend to ask for?) or you can just ask. “Is there a way you prefer to get updates from me?” is a completely reasonable question and most managers appreciate being asked.

For situations where your preferences and your manager’s preferences don’t align, it can feel like you’re performing or compromising something about your style by adjusting to a style that isn’t your natural preference. It’s not. Communication is only useful if it is actually received. Learning to translate for your audience (including translating upward) is a skill you’ll use for the rest of your career.

3️⃣: Bring a recommended path forward with every problem

Early on in leadership roles the instinct when something goes wrong is to escalate to the next level of management for help. “Here’s the situation” or “I’m not sure what to do about this” are natural communication starters we reach for, especially when we’re new and don’t yet have enough context to feel confident about a solution.

The problem is if that’s consistently how problems travel from you to your manager, the dynamic and the perception of your capability as a problem solver shifts over time. You become a reporter of issues rather than an active part of solving them. Your manager spends their time and energy reacting to your escalations instead of building trust in your judgment.

🛠️ The fix: this shift requires a little extra discipline: before you bring a problem, spend five minutes to build out an initial recommendation on a path forward.

Even if it’s high-level and even if you’re not sure the path forward is the finalized answer. “Here’s the situation, here’s what I’m thinking, I’d like to know if you see it differently” is a completely different, far more constructive conversation than “Here’s the situation, what do I do?”

Sometimes your recommendations will inform the solution, sometimes they’ll be discarded in favor of another path and that’s fine. The goal isn’t to always have the right answer, it’s to develop the habit of establishing a point of view before you share a problem with someone else.

The real examples underneath all three of these strategies is the same one: along the way (with plenty of help and reminders from my manager and mentors) I stopped waiting for my manager to notice what I needed and started saying it out loud.

Our relationship and collaborations got significantly easier as a result because they had the information they needed to help me, I had a clearer sense of what I was working toward, and we were intentionally working together instead of operating in parallel. Your manager wants you to succeed. Most managers do, but they can’t help you succeed if you’re not telling them what’s happening, what you need, or what you think. You own those pieces and the more seriously you take that ownership the higher your leadership trajectory will be.

Next week we’re getting into the territory a lot of technical managers find the hardest: when your team knows more than you do, and how to lead with authority when you’re not the technical expert in the room. That issue will be available for paid subscribers and I’m really excited to share it with you. (If you’re already subscribed at any level - free or paid - thank you so much. It means a lot and I appreciate you!)

If you’re not yet a paid subscriber, this is a good week to consider becoming one.

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I would love to hear your stories about how advocacy and managing “up” have been helpful to you in your career journey. If you have strategies or helpful hints for others, feel free to add a comment, Substack Note, or send me a message at contact.kaleigh@proton.me. I read every reply and answer as many as I can.

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See you next Tuesday,

Kaleigh

My first management role reinforced for me that everyone is navigating invisible challenges alongside their visible workload. Pandemic restrictions were still shaping how people showed up physically, emotionally, and in their relationships. Some of my team members were relieved to be back on-site in our engineering lab while some were still calculating risk every morning before they walked in the door. Many were holding heavy burdens at home they hadn’t mentioned at work. At the time, I didn’t think much about that context. Not because I wasn’t curious about the people I managed but because I was so focused on being a Good Manager ^TM and getting clear on the technical details that had made me successful previously. I ended up fully missing what was actually going on with the human beings on my team. Here’s what happened…

I was freshly promoted to management via a leadership development program and surrounded by peer managers who were also figuring it out the best they could. One of them shared a structured 1:1 template: what did you accomplish since last time we met, what’s up next for your project, what help do you need for the technical work. It was organized, practical, and resonated immediately with my background leading Agile teams. I thought: this is exactly what I’ve been looking for. I rolled the template out to my new team after scanning it briefly and updating it with our team name. I felt relieved to have a “best practice” to deploy and was excited to see the positive impact I was sure would emerge.

The first few 1:1s using the template were…fine. Everyone showed up with prepared answers, they were generally thorough, we covered the agenda but something felt stilted and wrong that I couldn’t quite pinpoint yet. The conversations felt scripted. The template had enough questions in it that we’d get to the end of the scheduled time and sometimes still have content to cover.

I was learning a lot about our lab, projects, and customers - and learning almost nothing about how the people on my own team were doing.

What I had done without realizing it was import a task management framework into a relationship-building context. No wonder the relationships felt stilted: the technical work was the priority; the person sitting across from me was not.

I made adjustments slowly at first: asking one open question before we opened the template and watching how people responded to it. What I noticed was that the answer to something as simple as “how is your week going?” told me far more about what the next thirty minutes should look like than any prepared agenda could.

Some people sat down visibly settled, ready to dig in. If there was a relative sense of calm, we could go forward with the agenda as planned.

Some people sat down carrying something. You could see it in how they answered the first question, if they deflected and how quickly, whether they made eye contact and what facial expressions happened. I tried to gauge this as best as I could, but I started to learn the agenda could wait and it was better for me to ask a follow-on question before assuming we should move forward with the agenda. Sometimes it was immediately clear that the meeting needed to stop being a meeting entirely and just become a conversation where I could offer support, a listening ear, or simply name a heavy thing I noticed someone might be carrying.

I had no framework for this at the time. I was learning to read it by feel, which meant I got it wrong and there were a lot of awkward silences, but the instinct I had was right. The first thing to understand in any 1:1 is not what’s on the agenda, it’s where the person in front of you actually is, emotionally. This data builds the frame for the rest of the conversation.

Since those first 1:1s, I built an actual framework to capture what I learned. It’s a way to check in with yourself before you check in on the agenda: I call it the Emotional Temperature Framework.

See below for a short summary - at the end of this issue you’ll find a link to a free PDF download with a more detailed version for your reference!

The Emotional Temperature Framework

Before starting your 1:1 agenda, take sixty seconds to read the room because the conversation your team member needs may be different from the one you both planned.

🟢 Green: Present and engaged. They’re making eye contact, their answers are direct, their energy is engaged. This person is ready to work. Proceed with the agenda.

🟡 Yellow: Slightly off. Something’s a little flat, a little distracted or fatigued. They’re doing fine, but they’re not fully present yet. Ask one more open question before you move forward. Give them a moment to arrive before making a decision about whether to proceed with the agenda.

🟠 Orange: Visibly tense. Stress, fear, or frustration is showing. This could be workload, something at home, or something else that happened today. The agenda is secondary. Acknowledge what you’re noticing; sometimes naming the tension helps it release.

🔴 Red: Distressed or overwhelmed. Something significant is happening and visible, strong emotion is present. This is not a day for project updates. Put the agenda away entirely. This is now a conversation to offer support.

FREE PDF: Emotional Temp. Framework

The goal isn’t to become, act, or function as a therapist for your team, in fact it’s essential that team members are reminded of any Employee Assistance Program-type resources available to them and encouraged to access them at any point, not just when they are in distress. The goal is to stop treating 1:1s like status reports and start treating them like the trust-building opportunity they actually are.

You don’t have to be a mind reader to successfully apply this framework, but it does require you to pause and be aware of what you see, hear, and feel in the energy coming from the other person in your 1:1.

In the end, the 1:1 template my peer manager sent me wasn’t the wrong resource, but I needed to be more thoughtful about how I and my team chose to utilize it. The technical work still matters, of course, but the hardest part of this job —the part that determines whether the technical work gets done at all — is ensuring you are building trust with the awesome, brilliant human beings making the technical dreams possible.

The Emotional Temperature Framework is also included in The Manager’s Conversation Toolkit — a set of tools built for the exact moments no one prepares you for. The full Manager’s Conversation Toolkit is available instantly to paid subscribers. Paid subscribers also have access to it via the pinned post at the top of the subscriber section so it’s always easy to find. It includes four full 1:1 conversation templates built for the exact moments no one prepares you for.

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I would love to hear about your strategies for running effective 1:1 meetings with your teams, your experiences reading the emotional temperature of your fellow human beings, and how you care for yourself through it all. Please feel free to add a comment, Substack Note, or send me a message at contact.kaleigh@proton.me. I read every reply and answer as many as I can.

See you next Tuesday,

Kaleigh

Hi and welcome!

You’re now a paid subscriber: thank you, seriously. Below is a link to the first thing I owe you: The Manager’s Conversation Toolkit.

This is a pinned post that will always be in your subscriber feed. It’s not going anywhere.

The Toolkit lives in Notion. If you open it via the link below and can’t edit anything, that’s normal since the shared version is read-only by design. To get a fully editable copy in your own Notion workspace, hit the “Duplicate” button in the top right corner on the Notion page. You’ll need a free Notion account if you don’t already have one, but that’s all you need to get started.

Inside the Toolkit (linked below) you’ll find four ready-to-deploy 1-on-1 conversation templates for the situations that are hardest to walk into without a plan: career development, performance discussions, navigating change and ambiguity, and rebuilding trust. There’s also two bonus frameworks included: one for reading a team member’s emotional state before a 1-on-1, and a second guide for what to actually say when someone on your team is struggling (including what not to say, which is definitely the tougher list).

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In late 2020, I got the “Congratulations, you’re getting a promotion…into management!” phone call. A few days later I found out I’d be waiting for that promotion to become effective for six more months.

During a global pandemic, many paths for career development were effectively frozen and while a six month delay wasn’t ideal, slow progress was still progress. The leadership development program that would make my promotion official needed time to fully negotiate, approve, and place our cohort of new managers into assignments. The logic made sense and I tried to find comfort in knowing there was a plan while navigating the emotional roller coaster of a ‘hurry up and wait’ reality.

I’d love to tell you that I spent those six months carefully preparing, reading leadership books, and writing a vision for the manager I wanted to become.

What I really did was spiral through the same questions on a loop. How would I stay authentically ‘me’ when I went from individual contributor to manager? Who would be on my new team? What if their technical expertise was in areas I knew nothing about? What would I tell my current teammates? (The people I was leading as an individual contributor, who had no idea I was leaving.) Would my senior manager be open to teaching a new manager? There were so many layers of work-related uncertainty stacked on top of the outside-of-work uncertainty that was overwhelming so many people during the pandemic and with every painful rotation of the spiral I felt less and less anchored. It was pretty rough.

I started my first management assignment six months later in mid-2021 and transitioned from working fully remotely to fully on-site in an engineering lab environment with some of the smartest, strongest human beings I’d met. My team included experienced engineers and techs whose expertise in some areas outpaced mine by decades. My senior manager received me as a brand new manager and made the best of it with dry humor that broke the ice and made me feel glad to be there. However, it didn’t change the fact that I had absolutely no idea what I was doing as a manager in the beginning.

Even as a person with a reasonable level of self-awareness and curiosity, the leadership development resources available to me at the time really only prepared me for the basics of being a manager: how to run a bare bones one-on-one meeting, how performance management processes work, how to sign a time card, and when to call the fire department. What they couldn’t prepare me for were those same, persistent questions that continued to loom in a corner of my brain every day in those first months, plus a new one:

“If I’m not a technical expert in the room, how can I be of help to this team?”

It took me a while to find my footing and I sometimes feel I’m still finding it, but I gradually found my way out of the question spiral and back to my sense of self. What I’ve learned since (from my own transitions and from watching others step into management roles) is that the feeling of disorientation is universal. The spiral is normal. Navigating the gap between “I’m a manager now” and “I actually know what I’m doing” is not a failure of preparation, it’s just what the transition looks like from the inside.

So if you’re in a role transition right now: waiting to start, newly started, or six months in and still wondering if anyone is going to figure out that you are in fact winging it, below is a framework I wish I had for that first transition. Not a roadmap, just five questions worth sitting with when you’re in the spiral and need some help to climb out. The good news is, these questions are also valid for any later role transitions, so when that promotion to the next level of management comes…you’ll be ready!

Five Questions for Leaders During Role Transitions

1️⃣ What expertise did you earn that didn’t disappear when your title changed?

Technical depth doesn’t evaporate when you become a manager, it becomes context: for making calls, for knowing when to push back, for earning credibility with your team. You didn’t leave it behind. It’s still yours.

2️⃣ What are you most afraid to admit you don’t know yet? Say it out loud, even just to yourself.

Something shifts when you name this directly, even privately. It’s harder to spiral around something you’ve already looked at and acknowledged.

3️⃣ Who on your team needs you to see them as a person before you ask them about the project?

This is the shift that changes everything early on. The technical answers aren’t what your team needs from you right now, they need to know you’re paying attention to their needs as human beings.

4️⃣ What can you actually control today? Name one thing specifically.

Not “the situation.” Not “the culture.” One thing. Identify it, then work on a path forward.

5️⃣ What is still recognizably ‘you’ in this role?

A role transition changes all kinds of things but rarely changes everything. Finding what’s continuous: your instincts, your humor, the way you explain a super complex problem, is how you stay anchored while everything else shifts.

These questions don’t have to have clean answers, that’s valid and normal. They’re check-ins, not solutions. Something to return to when you’re feeling overwhelmed, unsure, or like you’ve lost your sense of self.

More good news: you got this and you’re not lost. You’re just in the middle of it and you’re not alone.

If you want more tools for the conversations and moments that are hardest to navigate as a new manager, The Manager’s Conversation Toolkit was built exactly for that. Paid subscribers get access immediately and maintain access through the pinned post at the top of the subscriber section.

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I would love to hear about your first management / leadership assignments, your strategies for getting out of a spiral, the ways you stay grounded in moments of uncertainty, and the things you wish someone told you before you became a manager! Please feel free to add a comment, Substack Note, or send me a message at contact.kaleigh@proton.me. I read every reply and answer as many as I can.

See you next Tuesday,

Kaleigh