Leading Up to a New Boss

While there are different situations that result in a new manager, there are some common approaches you can use to ease the transition, build a strong relationship, and get off on the right foot.

The title of this piece provides its basic message: “Yes, this person is your new boss and has the responsibility to onboard you, but you abdicate your leadership role if you wait for them to take the first step.” One of the secrets of all successful leaders is that they know they need to lead up, as well as down and out.

There are of course different types of new bosses. Sometimes you take a new job with a new organization and are the new kid on the block. Often you’ve been promoted but it's to a position in your current company, but in a new division. Perhaps your old boss left and a new one has been hired. Maybe the most challenging situation is you were in the running, but did not get selected. And to add an even more challenging wrinkle to this, perhaps your new boss was formerly your peer co-worker. Ouch, that will pinch an ego. More about each of these situations later, but let’s first take a look at steps you should take regardless of which of these new bosses you find yourself leading up to.

Update your Self-Profile

Hopefully you have a good working knowledge of your strengths, weaknesses or development needs, what you are currently working on to improve, what you like to do, and what you find yourself avoiding. If you haven’t had a thorough 360 assessment lately, it’s probably not the best time to get a fresh one - you just met the boss and their assessment will be essential, so best to wait a bit. In the short run do a simple self-assessment. These are the questions to think about and record:

  • What do you do well? What are your strengths?

  • What strengths do you need to develop in your current position in order to succeed?

  • What weaknesses do you have and which ones will be more glaring in your current role?

  • How would you characterize your leadership style?

Once you are comfortable with this, give it to a work colleague that you know and who knows your work. Best if you know that they will tell you the truth about things. You will need to specifically tell them that this exercise will be most helpful if they are completely candid and direct. Take their input and develop a two page statement that characterizes you. For the time being there is nothing to do with this yet.

First Conversation with the New Boss

Beyond the basic meet and greet chat, this is the first substantive discussion you will have with them. What you want to know is what success looks like for you in this new position. What are the outcomes that you need to focus on to develop and deliver? As much as possible get a sense of timeframe and performance metrics without being too narrowly reductionistic. It's likely that the boss has some ideas about what they want from you, but may not have thought about it in detail and expects that you will provide these details. Depending on how familiar you are with the work and the organization, this first talk may be more of a two-way conversation. But if you are new to the team and the work, it will be more listening and coming to understanding then guiding. Regardless of whether you are familiar with the situation or brand new, a great ending question is asking for the names of three or four other people you can connect with who will have some insight into your new work. This will improve your understanding of your work, begin to broaden your network, and enhance your strategic framing of the work and your job.

Developing a Sense of your Boss’s Style

This first talk should have provided you with some valuable information about the preferences your new boss carries. Here are some categories to pay attention to:

  • Do they seem more like a big picture person or one more focused on the details?

  • What strikes you as what they value more: the work or the relationships?

  • Is their personality more quiet and reflective or more engaged and demonstrative?

  • Do deadlines and performance seem to hold their interest more than a thoughtful style that works toward doing the right thing?

  • Do they seem to push to the significance and impact of the work or are they more concerned about doing it the right way?

  • What do you think their style of communication preferences are likely to be: frequent and detailed, occasional and big picture, formal or informal?

  • How do they make decisions? Gather input broadly, but make them privately? Share information with the team and involve them in the decisions? Vary the style of decisions depending on the nature of the decision?

  • How do they handle conflict? Always confront it head on? Avoid it at all costs? Try to reach a shared solution that everyone can live with?

Make sure you write down your impressions of these from the first meeting and let the notes evolve as you develop a better picture of them and how they like to work and what that means for you.

Checking the Picture

While the boss’s view of the world will evolve over time and you will have some sense of this in the first month, it’s always helpful to check with them to ensure you have a good understanding. The easiest and safest one to check is communication preferences. After a month or so, take the occasion at a scheduled one on one meeting to reserve five minutes to discuss communications. You share with them how and why you are communicating - style, frequency, focus, and ask them if they find this approach useful and what they need. Hopefully they will value this from you and even more importantly they will give you some input on fine tuning.

Substantive Feedback on your Work

This should not be done sooner than your three month anniversary and no later than six months. Your boss may already be providing you with feedback that is timely and valuable and if that is the case, no need to schedule something separate. But if not, develop a short list of questions to guide their input. Some to consider:

  • Are you getting the performance from me that you expected? If not, what are the priority areas that I should address?

  • Is the quality of my work reflective of what is needed for our team?

  • Does my work demonstrate an understanding and appreciation for the strategic context of our team’s work and the organization's direction?

  • Do I seem to be fitting into the culture and work style of the team?

  • Am I putting the right amount of effort into the relationship values of our team?

  • What else would you like to see from me or have me emphasize in my work?

The scenarios for onboarding a new boss vary a bit and there are a few things for each of these different situations to keep in mind. These suggestions are in addition to the points above.

You stay the same but the boss is new

You have a lot of experience and insight that might be helpful to your new boss, but you will need to assess their style before you generously offer to “help” them. Just letting them know that you are ready to help in any way is important. Demonstrating that you can keep things confidential is essential. Speaking up carefully when needed, but only when it is warranted or asked for during the honeymoon period.

New job either in your company or somewhere new

Most of the suggestions above easily fit into this scenario without adjustment to the two other settings. You are the new kid on the block and need to demonstrate an active engagement with your new opportunity and boss.

You didn’t get the job and your former peer is your new boss

The hardest situation. Your ego is hurt and you are at a loss to stay or leave. Regardless, you go to the new boss, tell them congratulations, affirm that you had applied for the position (BTW, they already know this), let them know that you want to be 100% supportive of their leadership and that you are looking forward to building a new relationship, based on continued success for them, you, and the team. Then use the points above to actually build that relationship. The next time there is a leadership opportunity and your company is looking for candidates, you will be assessed on whether or not you acted like a leader in this trying situation.