One-on-ones with executives. @ Irrational Exuberance

Hi folks,

This is the weekly digest for my blog, Irrational Exuberance. Reach out with thoughts on Twitter at @lethain, or reply to this email.

Posts from this week:

- One-on-ones with executives.
- 'Drawing your three maps' exercise

One-on-ones with executives.

Often when an organization is going through some turmoil, executives think to themselves, “Ah, I should have some one-on-ones with the team so they can hear how we’re handling this.” On the other side, I frequently hear from folks who get nervous when they get these meeting invites, “The CEO/CTO/CPO/etc just scheduled a one-on-one with me! What am I supposed to talk to them about?” There’s no universal guide to this, but you can usually categorize these meetings into a small taxonomy of meetings, so here are a few notes on each variety and some general advice.

General Advice

Before surveying the taxonomy of executive one-on-ones, some high-level advice:

  • If you’re not sure what’s happening, let the executive take the lead
  • Try to figure out why the meeting is happening before you’re in the meeting. It’s much easier to prepare if you understand why it’s happening
  • Know that the executive will very likely have an agenda, but sometimes have no agenda at all, in which case it’s very helpful to have prepared ahead of time
  • You can influence their minds by asking good questions and by suggesting specific approaches with your rationale behind them
  • Good executives are able to effectively engage with your ideas/concerns/criticisms even if you phrase them poorly or deliver them with anger. That said, many executives are not able to hear issues raised in anger or with frustration. Even if you have good reason to be angry, it will usually undermine your point or get you categorized as “unconstructive” rather than effecting positive change
  • The advice on presenting to executives applies here as well

Fact Finding

The Fact Finding meeting is when an executive is trying to dig into something, usually a big opportunity or a big screw up, and they want to understand your perspective. There may be significant conflict with an organization. There may be a project that’s once again slipped by two months. There may be a recurring source of production incidents. Whatever it is, the executive has decided to get to the bottom of it.

In these meetings your most obvious goal is to answer the questions you get. You have two more subtle goals as well. First, you should try to fix their mental model if it’s leading them astray. For example, they might view a team you work with as underperforming, unaware that another team has consistently blocked their progress by changing the deliverable shortly before release.

Second, you should avoid unnecessarily inserting yourself into whatever problem they’re trying to debug. You may be asked to render judgment on peers, coworkers, a technology problem or whatever, and share your honest opinion, but don’t manufacture an opinion to share. Also try to be kind: my rule in this situations is to always assume what I say will be inadvertently shared with the person who it’s about.

Loyalty Check

The Loyalty Check meeting is an executive wanting to meet with you to determine if you’re bought into either a specific initiative or sometimes just bought into them. Generally these don’t happen at well-run companies, and I’d prefer to live in a world where this sort of meeting doesn’t exist, but I’ve experienced and heard of it too frequently to ignore it.

The executive’s goal in this meeting is to prevent interference with their current goal. Your goal with this meeting is to understand their plan, and to avoid coming across as an impediment. By the time an executive moves into loyalty checking mode, their plan is in flight to the best of their ability, so it’s rarely helpful to push back on the initiative. Instead, try to understand their perspective, and feel free to suggest nuance to how they approach their goal.

If you suddenly find yourself in one of these and aren’t sure what to do, ask open-ended, constructive questions until you run out of time.

Meet and Greet

The Meet and Greet meeting is a relationship building meeting without a well-defined goal. If you’re most comfortable with transactional meetings, this meeting will feel very alien because it has no transactional goal. Let the executive steer the session, and avoid the temptation to steer it towards a more tangible goal. Earlier in my career I found these meetings quite unnatural, but I’ve come to appreciate them more over time: it’s much harder to get stuck in the drama triangle when you know the other people involved as humans rather than business archetypes.

If you’re nervous about this kind of meeting, prepare an unreasonably large number of general questions and ask away. The executive is trying to get to know you, so it’s fine to bring open ended questions about their career, family, hobbies or whatever you’d find interesting.


You’ll sometimes find yourself assigned an executive mentor. You may be confused about what will happen during the mentorship session. More awkwardly, in many cases the executive you’re assigned to has been told to “host a mentorship session” and doesn’t really have a clear goal for the sessions either. Some executives will also be delightfully prepared with good questions, but you’ll only know which you’re heading into after you show up.

To avoid the session turning into a meet and greet, come prepared with focus areas and questions. In almost all cases, folks who get a lot from non-peer mentors are diligent at preparing and extracting that value from them. Relying on your mentor to structure the relationship will usually end in a dormant relationship after one to three meetings.

The best way to develop focus areas is to spend a few minutes studying your mentor’s background, identify areas where you’d also like to accomplish something that they’ve already done, and develop questions digging into that. How did you get your first functional leadership role? What do you wish you’d done before managing managers to be better prepared for that role? Should I spend time developing as a mentor to move into a staff engineer role? And so on.

Skip-level meeting

Underneath the hood, skip-level meetings are really a fact finding, meet and greet, or mentorship session. If you’ve never met the executive before, then it’s almost certainly a meet and greet, and otherwise you probably won’t know if it’s a fact finding or mentorship session until after it’s started. Prepare for a mentorship session, and save the notes for the next session if it happens to turn into a fact finding session.

And with that, best of luck in your next executive one-on-one.

'Drawing your three maps' exercise

I get to lead a monthly session with Calm’s staff engineers. Some months that is mostly a Q&A, but I find the best sessions have at least some component of directed learning. For example, we recently did a session on presenting to executives, which we used to dig into a decision I’d just made that had frustrated several folks in the session. However, at this point we’ve already done sessions on most of the “operating at staff” topics from Staff Engineer, so I’ve been trying to dig up more topics.

Fortunately, I recently got the chance to read Tanya Reilly’s The Staff Engineer’s Path, which is well worth a read (and is readable today as prerelease on O’Reilly’s online platform). The second chapter is focused on the idea of creating three maps to better understand your engineering organization: a locator map (where are you?), a topographical map (how hard is it to go nearby places?), and a treasure map (where are the places that are really worth going?). I thought this would be an interesting exercise to run as a group, with each of us taking ten minutes to create our own three maps, then sharing them out.

The instructions we followed were:

  1. Using one color, create your locator map, describing the key teams (e.g. Data Engineering, Quality Assurance, Customer Success, etc) and platforms (e.g. Content API, CI/CD, user authentication, analytics, etc) that you work with
  2. Using a second color, add topographical details to your locator map: draw in mountains where there is friction or little communication, add rivers where there’s a fast path to collaboration
  3. Using a third color, add treasures: where are the very high potential projects, capabilities, initiatives and relationships that could unlock something special? (Some folks also added hazards to their map, which are sort of anti-treasures. Generally any hazard can be converted into a treasure with a bit of creativity, so I think they are legitimate treasure candidates.)
  4. Explain your map!

Generally, this was a fun exercise, and the shareout was exceptionally interesting. That said, if I were to try this again I would probably try it in three phases, along the lines of: first session, draft your locator map, finalize it for the second session; second session, draft your topographical map, and so on.

One of the powerful things about maps is they contain so much data (this is one of the reasons what Felt is doing is so interesting to me), but I also found that trying to work through both the nouns and their physical relationship to each other was too much to get right in one pass. You really need time to iterate before the map gels. For most folks it was obvious within a few minutes that their map was wrong somehow, and doing the exercise within one session didn’t provide enough time to fix. Conversely, maybe that’s part of the value: sometimes an exercise that makes it abundantly clear that you can’t do a good job is a powerful way to break through uncertainty.

Anyway, it was a fun exercise, and I expect to extract more from the book as I spend more time with it.

That's all for now! Hope to hear your thoughts on Twitter at @lethain!

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Will Larson · 77 Geary St · co Calm 3rd Floor · San Francisco, CA 94108-5723 · USA

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