Why Startup Teams Resist Hiring a New Leader, and What to do About it

I’ve run across this situation with startup CxO coaching clients three times in the past week, so it felt like a good time to write about it…Here is the scenario: You realize that you need to hire a more experienced leader for an existing team, and there is lots of resistance to making the hire: the team doesn’t see the value in bringing on someone more senior, they think it will ruin their existing freewheeling culture, or they are confused that you want to replace a leader who is well-liked (but not performing well).Here is the deal: they often don’t know what a great leader would look, sound, or feel like, or what they would contribute to the team. Early hires tolerate uncertainty & chaos well, and value a lack of structure. To them, you are “ruining” a great thing. They have heard (or lived) the horror stories of bad managers, so they value strong individual contributors who can organize people around them reasonably well, and who primarily represent the core values & beliefs of the team. You, on the other hand, are looking for a solid people manager who will provide some more structure, accountability, & mentoring, who will contribute to a broader strategy and to the exec team, can act more autonomously, and who will balance the demands of the business with the needs of the team.You’ve announced that the hire is underway, you’ve written a job description, and you’re bringing in candidates. The team interviews possible leaders, and because they can’t actually envision what a more skilled/senior leader would look like, they screen for what they would look for in a peer (ability to do the hands-on job of senior individual contributor is usually what they look for), and overlook the qualities that would make them a great leader: people skills, ability to lead a team in making a decision, planning, accountability, and collaboration with peers to solve complex company-wide problems. The post-interview meetings devolve into arguments about what you’re looking for, and you start questioning your sanity, especially if you haven’t hired for this role before. You feel like you’re totally wasting your time talking to the team that’s arguing about this, and you wonder if the drama will ever end…The assumption that most drives people nuts about this one is that they dearly want it to be a collaborative process; they value getting the input & buy-in from those around them, and they can’t understand why the team won’t fall in line and help with the hire.I can think of at least two paths to follow, both with pros and cons…If you have other thoughts, I’d love to hear them in the comments.

(1) Context Setting, Conversation, & Tolerance for Disagreement

Realize that you have a vision of what a different level of leadership will bring to this team that they may not be able to see (especially if this is early in their careers). It actually helps to state up front: “I am not expecting to get 100% agreement on this hire; I want your input, but will be making the decision I think is best for the company, even if some of you disagree.” This frames the conversation in a way that allows them to contribute, but without the expectation that you’ll drive toward perfect consensus.Hiring a leader for this team can be an opportunity for learning, but one that will require some patience on everyone’s part. You will have to explain to the team what you are going for (you’ll likely have to explain it several times), and why. If you have anyone at all on the team who has worked for a great leader, and sees your point, this is the opportunity to speak to them privately, and ask them to help make your case. Even one person on the team who is highly respected can really help turn the tide here.As you make your case for the new leader you want, be careful not to insult the existing team. They have (hopefully) been doing the best they can with what they’ve got, and letting them know this is a punishment for failure is a quick way to alienate them all. I like to think of bringing in a leader like this as raising the leadership maturity of the team. You can’t blame them for not practicing what they don’t yet know.The team often wants to know why you are not promoting someone on the existing team; they look at this as a door closing, rather than a door opening. Your job is to explain that you’re looking for at least one person who has hands-on experience at a senior level, so that everyone can learn what that looks & feels like. This person is a potential mentor for other aspiring leaders, but without this hire, the maturity of leadership on the team won’t advance. This is especially true of millennials, who are often seeking bigger titles without an understanding of what is required of a leader at a higher level. You should be looking at “what is best for the company & team going forward”; they may initially be looking at “what will feel best to me right now.“They will poke at you, hoping that you’ll back down. Stand your ground. You will need to explain the difference between hiring an expert individual contributor, and a skilled leader (who may lack the on the ground skills they find valuable). If YOU were ever in the situation of doubting a leader hired above you, you can empathize with their confusion and frustration, and this will help. If you’ve had to hire a more senior leader for another group, and it worked out despite initial resistance, that story will be helpful too.This will not happen all in one meeting; it will be a series of conversations where you discuss the merits of different candidates, why they saw one thing, and you saw another. If you win over anyone on the team, you’re making progress. Give everyone a voice, but feel free to reframe things in terms of what you are actually looking for. Some of their feedback will be valuable, and some will not be. Listen for and acknowledge anything valuable. If someone digs in and starts to rant, it’s fine to say you’ve heard them, and you get that they disagree, but you don’t want to spend more group time talking about it. You may have to excuse one or more people from the process. It’s messy, and that’s just part of the deal. Don’t expect compliance.You will invest more time upfront, but what you potentially gain is a team who trusts that you’ll include them in the hiring process, feels that you value their opinions and their insight, and understands (at least to some degree) what their new leader will be contributing. You also get feedback from the team on how they think they will do with potential leaders (which you continually have to filter for what is valuable to you and what is not). So, bigger time investment, more frustration, but with a possible payoff in trust and understanding from the team.You will continually encounter resistance. That resistance is the team’s fear of change. Acknowledge that they are uncomfortable, and keep going. Don’t get discouraged if the team isn’t cheering for you. Anyone who is going to quit because you hire an experienced leader is not someone you can afford to keep on the team.

(2) Get it Done and Explain Later

Another possibility is to interview candidates without the team, involving only other people in your organization who really get the value of experienced leadership, and bring in the team at the end of the process. You can start this way, or sometimes you evolve to here as you realize the team is not really cooperating, but pitching a fit every time there is an interview. This is a hard sell if your company places a high value on participatory decision-making; people may expect to interview (and have a say about) their potential manager.This is a reasonable alternative when you know the team will resist ferociously, and get sidetracked agonizing about the leadership change rather than doing their work, or when you know you don’t have the patience or time to have multiple conversations about it throughout the interview process.The upside is that the process is faster, you may save yourself and others the frustration of heated conversations about candidates where you’re continually having to offer context about what you are looking for. The folks on the team don’t make themselves crazy interviewing and discussing lots of candidates, but also don’t get the value of seeing the process firsthand. The downside is that you lose the potential insight you would get from a well-informed team, and more important, you sometimes lose the trust of the team, and have to rebuild it as you put the leader in place. So, the front end of the process is faster & easier, but on the back end, you have to spend some time with the team introducing this new leader, explaining why they were selected, and explaining why the team did not get much of a say in the process.Often the discomfort & disagreement is packed into a very short timeframe (the end of the hiring process, when you are about to make an offer, or when the leader has just accepted), and tends to be more intense & agonizing. You want to celebrate that you finally found the leader who is going to do amazing things, and the team is (understandably) in shock, realizing they are about to work for someone that they barely know. For some people, the sense of betrayal & frustration is overwhelming, and you end up having to talk them down from the ledge. This option requires patience & extra empathy at the end of the process; it will feel out of sync for you, but you have to recognize that it’s totally new and a big deal for the team.

Special Case: Replacing the Existing Leader

There is a special case when you are replacing an existing leader who would prefer to maintain control of the team themselves; everything above also applies, but you have a pre-hiring step where you talk to the leader, let them know why you’ll be hiring for this leadership role (ideally you’ve been giving them feedback for a while so this is not a total surprise). There are two possibilities: that other leader is going to leave (quit or be fired), or they are going to stay and agree to support the new hire. Unless you want them gone, I would ask them to make a conscious choice: decide to leave gracefully, or agree to fully support the new hire as a member of the team (no grumbling, undermining, etc). Once you complete this step, you once again have a team you are hiring a leader for. There are rare cases where you may choose to hire a new leader behind the scenes and fire the old one at the last minute; I’m not a big fan of that. The secrecy ends up feeling creepy, and if the leader is so bad you’re going to fire them, why keep them around? Why make it harder for the new hire to step into a messy transition?Either way, if you are new to hiring for this position, it will be a learning process for you. As you interview each candidate, you will start to get a feel for what the different types of leaders feel like, and eventually you’ll zero in on someone who feels like a great fit, in knowledge, skills, and culture. I’ve seen this take between weeks and months (depending upon the candidate flow, and how much this is a learning experience for the final decision maker), but you will come to a point where you “get” what you’re looking for, and start to feel more confident.For some hires, it’s crystal clear which one of these strategies is going to work best, and for others, you will migrate from (1) to (2), or even from (2) to (1). What I most want is for you to understand what the options are, and their respective pros and cons, so you can make a well-informed decision about what will be best for this team. Either way, there is going to be some context setting and some hard conversations, but hopefully you will end up with an experienced leader who grows & leads the team in ways they could not even anticipate—that’s the ultimate win, however rocky the road to getting there.If we’re working with a coaching client going through this, here is what some of our conversations around this topic might look like:First, evaluating the situation, talking about the pros and cons for this team, and deciding which strategy to take.If the client decides to involve the team in the hiring process, we talk about which team members are most likely to be allies, how to approach them for help early on, and how to present what is happening. Ongoing coaching alternates between helping the client to be patient as people slowly shift their perspectives (or don’t), and helping the client distinguish between feedback that’s useful to the hiring process (ex: candidate didn’t listen to interview question and answered with “canned” speech) vs. feedback that is not relevant (candidate isn’t an expert at writing Java code). The biggest challenge is that the client loses confidence in their own perspective and their judgement, or fail to see progress, and loses patience with the process.If the client chooses to hire without involving the team, early focus is on selecting others within the organization to help with the hiring process, and preparing questions that elicit information that will uncover if the leader is a good match for this particular team, and helping the the client strengthen their own sense of what they are looking for as more and more candidate are interviewed, and the qualities that are most desirable come into focus. Once someone has been selected, we talk about how/when to introduce the team to their new leader, finding allies to help the process go more smoothly, and preparing the client for the team’s reaction (which may be negative initially, even when you’ve made a great hire).In either case, developing the capacity to talk with the team about their concerns and fears without reacting yourself is a huge advantage. Finally, we focus on figuring out what support is necessary to make the new leader successful, and check in to see how they’re doing, and what course corrections are necessary along the way.What else have you seen work well (or fail spectacularly) in this kind of situation?(Extra thanks to Dale Larson for reviewing and editing)