Career ladder for executives: a clarifying expectations document

Newsflash for CEOs and CXOs everywhere: executives are people too. They need to understand what you expect from them as much as individual contributors and managers do. If members of your executive team don’t know what’s expected from them and spend attention cycles guessing, how effectively will they lead their orgs?

A message to all my executive friends: if your boss isn’t setting clear expectations for you, it’s in your power to shape the conversation. State it’s important to you and offer to come up with a draft. Help them help you! I’ll be shocked if they flat-out refuse to work with you on this.

Why executives often don’t get clear expectations

Even in companies that have defined expectations (a.k.a. career ladders or competency maps) for their individual contributors and managers, it’s often the case that expectations of executives aren’t clearly defined. Here are some reasons:

  • “Executives are a very small group compared to the rest of the company, and effort goes into covering individual contributors and managers with expectations first.” While mathematically correct, executives presumably drive or destroy a lot more value through sheer responsibility for the rest of the company. Setting clear expectations for them is arguably more important.
  • “Executives sign up for goals / OKRs; that’s their expectations.” Goals at executive/company level are typically few, not a complete list, and, depending on how advanced your company is with planning, may not go beyond a quarter. You want to incentivize your executives on long-term goals and behaviors as well as on hitting quarterly goals. You also want to agree on the relative importance of goals and on what “below/at/above expectations” means.
  • And my personal favorite, “They are adults, they should know what they’re doing; that’s why we hired them.” If people spontaneously did what the company wanted them to do, we wouldn’t need managers. This observation applies to all levels of the hierarchy, including executives. Post product-market fit, one of the three most important jobs for a CEO is executive team recruiting / goal setting / alignment / performance management, as expressed in this excellent post by Ali Rowghani of Y Combinator. Same goes for CXOs who have VPs reporting to them.

There’s no good reason for not defining clear expectations for executives; only lame excuses. Stop making them and get to work!

How you can create an expectations document for executives that doesn’t suck

Executive expectations should be more bespoke than career ladders for individual contributors and managers at large. You can count executives on one or two hands, and they are collectively responsible for the whole company; it makes sense to put in the work to get their expectations right! Because of focused attention, executive expectations can be better than other career ladders in one important way: they can be written to be outcome-focused vs. purely behavior-based.

When creating expectations that need to work for multiple people in the same level/role, especially across functions, one naturally must default to describing behaviors (like “acts on behalf of the company first, team second, self last”) because outcomes we expect from all these people will be entirely different. When dealing with expectations for one person, we don’t have this constraint. There’s obvious advantages to writing outcomes into an expectations document: outcomes is what actually matters to everyone. With outcomes comes the opportunity to record the rubric for grading how good the outcomes were – take this opportunity!

Finally, collaborate on the expectations document. Buy-in is obviously a good thing here, so make sure expectations are vehemently agreed to by both sides and are treated kind of like a contract. In addition, the executive on the receiving end will have great ideas and knowledge of details that their boss doesn’t possess – tap into it!

What an executive expectations document can look like

Thanks go to my boss Zhenya Loginov who worked with me on this document. Here’s a mildly sanitized version for a VP of Operations:

Some notes:

  • I’ve worked on exactly one of these documents, the one you see above. The result makes a lot of sense to me. Having said that, I’m by no means an expert on these though, so take this one with a grain of salt.
  • The nature of most of this document’s content is highly personal to one executive/boss pair at one company at one point in time. It should be mapped to your company values and desired traits. Use this as inspiration but come up with your own buckets, themes and cell contents. They need to sound like you speak and reflect what’s important in your setting.
  • Performance against these expectations should be reviewed in structured check-ins before factoring into formal yearly/half-yearly performance evaluation and career conversations/planning. Once we had this document, both my manager and I used it in formal performance review – I to write my self-review and he to consolidate peer, upward and his feedback for me into a downward review. Having this doc made the process so much fairer and simpler!
  • While no document will guarantee perfect understanding between two people at all times on such a charged topic as performance evaluation, I am happy to report that writing these expectations down and agreeing on them made me feel a lot more confident that I knew “the rules of the game” and helped me spend fewer anxiety cycles wondering how my performance was going to be evaluated.
  • I’m especially proud of the “team” section in this doc. I think it goes beyond the obvious (“team is happy”) and covers important yet non-trivial things like identifying and hiring for key roles in time. I think the “reputation” bucket is also neat: while it doesn’t formally factor into the evaluation, it’s a structured check on its validity. The short-, medium- and long-term distinctions in expectations are also awesome.

I hope this is helpful to executives and CXOs out there. Ping me if you’d like to talk through it!

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