- Sets the wrong goals. Self-explanatory.
- Obviously bad decisions are made. Sometimes a person is clearly in over their head when they make poor choices or unforced errors that others with the same role would quickly point out. For example, if a head of finance hires a regional auditor instead of a big 4 auditor for a company that is planning to eventually go public.
- Does not have a roadmap or plan for their area or function. Each function in a scaling organization should have a multi-year plan. This plan may be off or wrong, but once a company passes a certain scale and of revenue and people there should be a forward looking plan. What channels will the sales team use and how does that map to a team? What is the sales plan over the next N years? What is the product roadmap from the VP Product? The technical roadmap from the VP Eng? Marketing plan from VP Marketing?
- When you hire experienced executives the first things they often do (in parallel to getting the lay of the land and talking to a ton of people) are putting together an org plan, and putting together a time-based roadmap for their function.
- Misses commitments and is frazzled. Shows up late, is unprepared, does not plan ahead or come prepped for a meeting. Sends everything last minute for executive reviews or board meetings. Does not follow through in a timely manner or at all.
- Makes ongoing comments about overwork. “Maybe I will get to that in my free time – haha” said semi-sarcastically to indicate overwork is a not an OK response when asked to come up with an important new product plan, sales plan, or org chart. It usually means the executive either is not delegating enough effectively, or never hired a team strong enough to help them take on more.
- Can’t attract other senior talent. The biggest sign of a non-scaling executive is their challenge in hiring senior people to work for them. They often have difficulty articulating what each role on their team will do, how it differs from their own role, and what is needed for the function to outperform its goals. If an executive is unable to hire strong lieutenants to their team it usually means they are promoted beyond where their own experience or current abilities merit.
- Inability to hire senior people (either because the executive does not think it is important, or can not attract senior people) is a key tell that the executive can not scale and should be replaced. If senior people were in place beneath them and aligned in the right direction, there would not be strong scaling issues in their function.
- Do not think they need senior people on their team. When a company is ten people you do not need multiple layers of senior people. Similarly, there are functions that do not make sense to expand in many companies - for example you usually do not need a giant legal team. However, when a company is hundreds of people, senior bandwidth is needed under the executives driving core functions. If an executive's org chart & plan is largely junior people, it might mean a coming issue in team bandwidth.
- Does not have an org plan. Great executives constantly refresh their organizational map and plan. They plan ahead on key senior hires and how their team will matrix of coordinate with counterparts in other organizations. One sign of a too junior executive or one who may not scale is if their org plan only has junior hires on it, when it is clear the business will scale rapidly and more senior bandwidth is needed. It is the CEO equivalent of hiring “2 SDRs instead of a VP sales” when you really need a VP sales. Non-scaling executives hire a number of junior people and get caught flatfooted 6 months later when real scale is needed. For example, in the context of a multi-hundred person company if you have a VP Product who plans to hire 10 ICs but no managers, or a CRO without any plans for *real* VP-level reports.
- Usually you can tell you have hired an experienced executives if one of the first things they discuss with you is their functions future org chart. They come in prepared and know that people who work for them matter most for company scaling.
- The CEO is pulled into their function more than you should be. The whole point of hiring executives is to have people who are stronger than you take over a function, or so that you can delegate major items and expect them to be done well. If you are constantly being pulled in to help a function or to cover for an executive, it means they are in over their head.Examples of this for a VP Eng: You (the CEO) often need to deal with individual engineering team squabbles or recruitment alignment. Or you need to jump in on a technical issue or adjudicate a specific design.Examples of this for a VP Sales: You are needed to handle all the specific dealpoints on a negotiation. You are building the deck before the presentation to the customer. You need to be on many customer calls that could be handled by a senior sales leader.Examples of this for a VP Finance: As CEO you build financial models for the company because you do not trust the team to do it right, or the data they give you is often off or confusing. You need to do your own data pulls to get answers. Etc.There are lots of other examples. If you find yourself pulled into certain details or aspects of your executives roles that they should know how to run, the person is clearly in over their head.
- Other people keep needing to help exec more than usual. Startups are a team effort. However, sometimes you see an executive who needs too much help from others – they are not able to hire without someone pushing them to do it, or they need to keep pulling on the CEO or other leaders for every key sale or product decision. It is better to have an executive who is team focused on coordinates with others, but sometimes they can not do their role without help which means they are not scaling.