The Narrow Path to Success: Hiring a Player/Coach and Avoiding Disappointment

By Jeff Schwaber

January 11, 2022

I hear regularly from people in startups who are looking to hire a player/coach, most often for a role in Engineering, Sales, or Marketing. Plenty of founders out there don’t have enough money to hire a team for every area of the company and are hoping they can find that magical person who can be their founding engineer/marketer/salesperson who will then take over the area as the company grows.

The ideal player/coach unicorns, of course, will think through the strategy, ensure you’re doing all the right things for the business in areas like legal and compliance, listen to the customer feedback and change their plans based on it, and also, do the day-to-day work in their area, whether writing code or copy or calling prospects.

When someday we’re making more money, well, that person can also recruit, hire, build and manage the team, mentor and grow more junior employees, and keep rebuilding the strategy as we grow.

It’s certainly true that there are people out there who can succeed at this. It’s also true that this level of expectation on a hire means a lot of people hired into this sort of role end up disappointing the founders who hired them. There are a handful of ways to avoid that disappointment. Before we get to that, let’s go through the types of people who get hired as a player/coach and the ways that they disappoint. That’ll give us a good starting place to prevent this type of failure.

The four archetypes of the player/coach

First, we’ve got the A-player who wants to be a leader, aka the hopeful beginner. That is the person with a few years of experience doing the work who is looking for a way to jump over the hurdles that would be presented to them in a bigger company before they can climb the management ladder. If they can get some experience here, they can skip a level or more when they go back to the big company. Maybe they can learn enough to start their own company. Usually, the hopeful beginner is an individual contributor, like an engineer or marketer, who is looking to step up to strategic work, often because they’re tired of seeing the managers make what they view as the wrong decision. Sometimes, they’ve been a line-level manager before as well.

Second, you’ve got the repeated early-stager. They’ve been VP of this area for a couple of previous startups, but they hit some ceiling in those places and went looking for a new place to start over—maybe they don’t do well past 50 employees, or once they have to manage more than a dozen people, or they just get bored after a few years.

Third, you’ve got the excitement recapturer. They’ve been in management for a while, and they got tired of all of the politics, or they remember fondly when they used to do the work and want to give it a go again. These folks sometimes seem like the repeated early-stagers—every repeated early-stager was this person at one point, but many excitement recapturers will fail out of their second role rather than become repeaters.

Fourth is the big game talker. They seem pretty experienced from their LinkedIn profile, but their titles are often vague, such as Head of Partnerships or Integrations Lead. They can articulate well the aspects of both strategy and people and speak to the challenges of startups. They seem as if you could shape the role to leverage their previous experience or network well.

Despite the name, a player/coach is actually called on to do three roles: player, coach or manager, and leader. Because of this, they can and do often fail at one or more of these three roles.

One thing we have to recognize is that strategic leadership, coaching and management, and individual contribution are fundamentally different types of work. They depend on different skills and ask for different areas of focus during the workweek. Management and leadership, in particular, are not an obvious extension of being a great player. The most productive people don’t always make the best managers. New managers often fail out because they’re trying to still be individual contributors. Engineering ladders create a path for engineers that allows them to grow without having to become managers. Promoting a great IC (Individual Contributor) doesn’t guarantee you a great manager. In fact, if that’s the only characteristic you evaluated when promoting, you’re very likely to get a bad manager.

Avoiding disappointment: the transition from player to coach

The hopeful beginner is most likely to fail at the management or leadership tasks—they’ve usually been an IC, and this is their chance to step up to being a manager, team builder, and strategist, and they fail in lots of different ways here. They might be so focused on the details of their task that they don’t stop to notice that it’s not work they should be doing. When they hire other people, they may hire people like them rather than thinking through the team they’re trying to build. When they manage, they may just direct what to do and not care for their employees, or they may not even manage them, just assuming that, as they do, everyone can figure out what’s important and do it. They may not know what’s important strategically. As an engineer, maybe they ignore security or compliance concerns because they are focused on delivering features or because they don’t understand them, or as a marketer, maybe they focus on ads without thinking about the type of person the customer is or getting the message right. As a salesperson, maybe their focus on delivering this sale means they ignore the other leads in the pipeline, who get pissed off and go to a competitor, or they say yes to everything the customer asks for, even though the company can’t deliver on it.

The other characters are more likely to fall into the “being a bad player” camp. They’ve done the player role before, either recently or a long time ago, and they got to like the coach role because of the leverage, the work, or the support of other people. When they get back into the IC role, they don’t like it, can’t focus on it, or just don’t do it. They typically ask other people around them in the organization to fill in for them in a variety of ways. So your salesperson is asking for a constant stream of content and leads from the marketing team (or marketing intern, if that’s all you have) and is spending more time tracking the leads and numbers than on the phone. You don’t get many sales from all that time spent in Salesforce. Your engineering manager is checking in with (i.e., distracting) the one engineer working frontend five times a day and making sure everyone knows the latest status but hasn’t written any code or keeps expanding the technical design documentation for upcoming features while the current ones take forever. Your marketer has brought you three contractors they think are going to be an excellent fit for writing messaging and copy, building videos, and making logos but hasn’t sent out a newsletter in months, and the ads that are running are out of date and not bringing much in.

It makes sense that startups hope and plan for growth in their employees. Startups are an idea that they hope will take root and grow, and their people will grow along with them.

But it’s also wise to look at that hope as a risk and do what you can to reduce it. When it comes to hiring a player/coach who’s actually a player but is hoping to grow to be a coach, it’s more likely they’ll succeed if you can also provide them a coach who can help them. Do you have someone on staff identified as their mentor? Startups founders rarely have the time to support the level of growth you’re probably hoping for. Should you bring that in from outside through your network or a professional coach?

On the other hand, when hiring a player/coach who’s actually a coach, they’re more likely to succeed if you can provide them with someone to coach. Perhaps some of the IC work they need to do can be done by contractors, or you can commit to bringing in a junior employee soon. If what they are happiest at is strategy or teambuilding, ask yourself carefully when will you have enough of that work to keep them satisfied.

Unfortunately, lots of people trying to be a player/coach don’t seem to work out well. The cases where they do, though, tend to be players who had good coaches available to help them make the transition and coaches who could rapidly transition into hiring a team to coach.

Other perspectives on this topic:

• Alex Ezell on LinkedIn.
• How Kurt Warner’s Career Relates to Software Developer’s Performance: Players, Coaches, and Systems By cjhuitt (On Management Kaizen).
• How to Hire for Your Startup: The First 8 People You Should Hire By Skye Schooley (On Business News Daily).