Joining a new organization as a leader is hard. I have done this repeatedly throughout my career and I take great care in getting settled in and making sure I fully understand things before starting to make changes. One of the reasons I write these articles is so people can get a chance to see things from a different perspective to help them grow professionally. Today I want to talk from a different perspective about joining an organization as a leader. I want to talk about what to do when you have to hire your own boss.
I know that sounds a bit strange at first, but it is not. It is pretty common that teams need to develop new leadership and sometimes the existing people in the team do not have the skillset, the experience, or the mindset to fill a leadership role internally.
Some companies try to give battlefield promotions to fill the gaps which tends to work out in the long term but generally has a pretty bumpy short term period where a new leader makes some unfortunate mistakes. I know this because I have gone through a few battlefield promotions and have made some of those mistakes.
For a variety of reasons, other companies are not comfortable with that approach and choose to look outside to recruit new managers, directors, and executives. Today we are going to talk about what that means if this is happening at your company, and the manager, director, or executive in question is going to be directly above you.
The first time this happened to me was very unpleasant. I found out in a company meeting that the person I was interviewing to be my peer was going to be my manager. I can assure you this is the worst possible way to discover you have a new boss. I was gone within a year, and if this happens to you, I would wager you would find your trust in your employer so sufficiently violated that you would likely want to leave too.
Companies today are hopefully much more transparent than twenty years ago. It stands to reason that if you are hiring a new manager into your organization, you are going to have some of the people who will be reporting to that person participate in the hiring process as interviewers. It is generally a sign of some sort of organizational problem if that is not true. It might be the case that you are being interviewed to solve some of those problems.
For the sake of the rest of this conversation, let’s assume you are participating in the hiring process. So what should you be thinking about?
Why am I getting a new boss from outside the company?
This is a perfectly valid question. If it is your goal to move into engineering management, it is easy to get upset or frustrated to hear you are hiring a new manager from outside the company. You do deserve an explanation about what the reasoning is, and what gaps you may possess that prevented you from being considered for the role.
In times that I have been interviewed by potential direct reports, I have felt their ire at being passed over for an outsider even in the interview process. I totally understand it and accept it. At that point the challenge for me is to help someone accept that this could be a good thing and could present a learning opportunity to make a transition into a new career smoother and also more efficient.
It is worth noting that if this decision has already been made, you are likely not going to be in a position to reverse it. I have seen some people try to fight by vetoing every candidate that comes in.
That is a bad idea. What will eventually happen is that it will be noticed, and you run the risk of being removed from the interview process.
I would add that if you are getting a new boss and you are removing yourself from the process, either you will wind up with a manager with whom you have had no say in selecting, or you might find yourself in the crosshairs as a problem to be solved by a new manager when it is revealed that you objected so strongly to all of the candidates. Whether or not that is fair, you might find yourself in the spotlight for a while from your new manager while they try to figure out why you objected so strongly and how much time they want to spend in helping you through that process.
What should I be looking for in a new boss?
Now that we have established that just saying “no” over and over is likely a bad idea, you should try to figure out what it is you want from a new boss. There are going to be some easy and obvious questions you can ask which will likely result in basic platitudes and reassurances. When hiring anyone, I always recommend asking best case scenario / worst case scenario questions from candidates. My goal is to learn default behaviors and what I can reasonably expect.
Here are some good questions you can ask a potential future boss:
- Describe how you helped a previous employee get a promotion.
- How long did the best performing engineer work for you?
- Tell me about the best employee you ever had and where are they now?
- What do you do when an employee is struggling in their current role?
- How do you define success as a (manager or director or vice president)?
- What is your greatest leadership accomplishment?
If you can get them to talk about past successes with their teams, or past failures on their teams, it is a good way to learn about how you might be working together. It is important to learn about positives and negatives here. I remember having an uncomfortable conversation with a senior engineer when interviewing for a vice president of engineering role. They had asked me the question “how do I decide when I have to fire someone.” I described my thought process about trying to help people find their best role and how many opportunities make sense for someone who is struggling before putting them on formal notice that there is an issue there. I could tell at the end of that explanation that they were horrified by my answer. If asked, I think I would still answer the question in the same way because it is a serious responsibility to make team adjustments and you should have a plan to do your best for both the individual and the company to try to make things work.
I am pretty certain that individual vetoed my candidacy for a number of reasons, including multiple days of “this person looked at you on LinkedIn” which ended when I got the “we decided on a different direction” email. I am pretty sure each of us felt like we dodged a bullet of some kind.
Why is this person interested in this job?
This is always a tricky one to unpack. People have the strangest motivations for wanting a job. I always like to understand what they are. You should always ask your potential boss why he wants that job. I also recommend asking what they plan to be doing in five years time.
I would be here for hours if I was to list every motivation that people have for wanting a new job or wanting a particular job. Suffice it to say you should ask yourself if you like their answer.
I have taken a good number of jobs via referral because I am lucky to have many smart friends that I have greatly enjoyed working with over many years of my career. I am always happy to help them solve their problems.
If you can establish someone’s career plans and trajectory, that can help you determine whether or not you could have a great working relationship with them. “I need time-in-role as a Director of Engineering” suggests they are focused on getting promoted which has its good and bad parts. “I need experience leading larger teams so I can run a company division some day” is a different way to say the same thing, but it is a better answer. The latter candidate is fixated on team growth, and the prior candidate might be willing to do more upwards management to get a promotion.
How can I help the candidate that I like get hired?
After speaking to a few candidates, you might find yourself in the position of liking what you hear from one candidate over another. Please make that known to the decision makers who are driving the recruiting process! They may ask why, and your feedback might help steer them towards supporting that, especially if multiple people are saying the same thing.
If you find you have a genuine connection with a potential boss during an interview, you should definitely try to paint a clear picture of what life is like at your company, and that you are interested in supporting their candidacy.
I would also recommend reaching out to them to establish a more direct connection after the fact. After all, if your company does not hire this person, some other company probably will. It might be the case that there will be a potential future overlap.
It might even be shortly after they hire someone you don’t like as your boss. In which case it might be worth reaching out to them to see if they are hiring, considering you are probably about to start having a less pleasant time at work.
What can I expect from a new boss?
Now that we have explored a framework for hiring a boss, and all of that is finished, I should let you know that for the first while, you shouldn’t expect much from a new boss. It takes some time to get settled into a leadership role and to understand what is important and what is not important. Every organization has its own wrinkles and curiosities.
While I generally set up a weekly 1:1 with all members of a new team, it would be a good idea to ask your new boss if there is anything you can do to help them. Offer them a weekly AMA to help them get settled in and learn “the little things”. Figure out a list of people they should be getting to know and ask if they want you to facilitate some introductions.
The ultimate thing I do as someone’s boss is to figure out the best way to make them more successful. I have found that the sooner I have gotten successful in a leadership role with the help of my team, the sooner I can get down to the business of helping them become more successful.
Thank you again for reading. Something something social. See you again next week!
