How to get more headcount.
One of the recurring challenges that teams face is getting headcount to support their initiatives. A similar problem is the idea that a team can’t get a favored project into their roadmap. In both cases, teams often create a story about how clueless executives don’t understand why their work is important.
I understand why dumb executives are such an appealing explanation to problems: it fits perfectly into the Karpman drama triangle by making executives the villain and the team the victim, but I generally find that these sorts of misalignments are the result of basic communication challenges rather than something more exciting.
When there’s significant misalignment between a team and an executive, my experience is that it often manifests in discussion about a particular project, but it’s often rooted in a much broader topic rather than whatever is currently being discussed. Because the disagreement is about the larger topic, there’s no way to resolve it while discussing the narrow project at hand, and teams struggle to make progress because they’re arguing on the wrong layer of context.
To solve disagreement, the general hierarchy of alignment is:
Do we agree on the problem to be solved?
e.g. We’re having too many incidents and it’s impacting user perception and developer productivity.
Do we agree on the general approach to solving that problem?
e.g. We’re increasing end-to-end coverage and rejecting PRs that reduce coverage.
What evidence do we have that the team is executing well today?
e.g. Here are metrics on: how many user-impacting incidents we’ve had over time, how we’ve increased end-to-end coverage over time, and developer survey feedback on incidents from the last three quarterly internal surveys.
Alignment on the particular topic at hand: headcount, roadmapping, prioritization of a specific project, and so on.
e.g. To speed up further work on this, we’re requesting two more engineers.
If you are misaligned on any of the first three topics, addressing the fourth project is folly. For example, if the executive believes that your team is not executing your current project well, then they won’t believe that giving you more headcount is useful, because you’re already screwing up. To convince them to approve a headcount request, you need to first find evidence that your team is doing good work today.
Similarly, if the executive doesn’t agree with you on your problem or general approach, your headcount request is dead in the water. This is one of the reasons that I see bottoms-up “team mission” initiatives fail so frequently. Teams define their mission, and then tell executives what they’ve decided to focus on, but that’s a general misunderstanding of why teams exist: teams exist to solve a company need, not to solve the problem that the team itself wants to solve. When teams lean on their self-selected problem or approach to defend to an executive why they won’t do something, they dig in on a foundational misalignment that prevents addressing more nuanced discussions like project prioritization.
The solution here is obvious, always make sure you agree on the problem and general solution, and provide evidence the team is working well. These can be an appendix of a document or appendix slides, and should take little to no time to prepare as the first two are core decisions for your team, and the latter is a set of metrics or plans that you should already be maintaining as part of operating your team.
If you refuse to engage on the first three topics, and skip to the fourth topic directly in aligning with an executive, then you are generally falling back to relying on social dynamics and executives’ general view of your prior work–what some might call politics–rather than having a joint problem solving session together. If you’re complaining about politics, and not taking the time to answer the first three, then perhaps you are inadvertently contributing to the political environment that you dislike.
As always when discussing challenges communicating with executives, it’s true that executives should get better at explaining where they’re confused or struggling with the rationale. However, it’s a lot more useful to simply get better at this yourself than to spend time bemoaning how executives could, as a universal group, improve their communication. I know a lot of people who improved their company or moved into more senior roles by improving their own communication. I know zero folks who did either of those by complaining that executives are bad communicators, although they certainly weren’t wrong about it!