Preparing for Meetings with New Bosses

During my career, I've often seen new bosses come into the workplace. It was always an opportunity to advance both my career and my agenda for the organization.

Sometimes the boss was several levels above me, as was the case when I worked at the Community Service Society of New York. David Jones became the CEO and Steven Krause the COO. My boss, Josephine Nieves, reported directly to both of them, and I reported to her. I often accompanied Josie to meetings with one or both of them, and was impressed by the amount of preparation she did for each meeting. Usually, we got the outcome we desired! More than that, I gave thought to how I wanted them to perceive me - as capable, responsive, intelligent, results-oriented, and strategic. I demonstrated this through my behavior in meetings as well as through my follow-up - and as a result have good relationships with both David and Steven to this day.

At City Harvest, I had many new direct bosses. These included several different Chairmen of the Board of Directors, as well as incoming Board members. I always met privately with each of them, and spent a lot of time strategizing before each meeting about what outcome I sought. I strategized with my coach and usually with at least one of my senior leadership team members. At each of these first meetings, I established the groundwork effective working relationships with each Board member and Chair. How effective? The proof is in the results. By building those relationships, I led City Harvest to its phenomenal growth in services, funding, and visibility.

I was reminded today of how important it is to be strategic about first meetings with any new boss, when I talked with an up-and-coming faculty member at a university where there are two new Deans in Departments with which he is affiliated. He wants to meet with each of them and wondered if it was appropriate. I thought yes, as long as he has a purpose for the meetings, and as long as he tells his direct boss that he plans to have the meetings and when they are scheduled. (This relates to the "no surprises" rule - one should never surprise or embarrass one's immediate supervisor especially with any of their superiors.)

In response to a question, he admitted he hadn't yet thought through what he wants out of the meetings. Certainly, he wants them to know who he is. The question is "why?" We spent a good half hour talking about that topic at the end of which he felt much more prepared. This is what I suggested:

In setting up a meeting with a new boss - either your own or one higher up the food chain - it's best to ask some key questions.

First: What's the purpose of the meeting? There has to be a clear reason to request a meeting, as well as a well-articulated agenda. Otherwise, the meeting will waste everyone's time. And you don't want to waste a boss's time; it just annoys him or her and casts you in a bad light. Having a clear purpose makes it easier to get a meeting in the first place, particularly if the new boss has an Executive Assistant as "keeper of the calendar," aka gatekeeper.

Setting a goal is the first step toward developing a plan to actually get there. the purpose could be "getting to know you," it could be to raise some topics, or some combination of the two (as in my friend's case).

From these purposes flow additional questions.

Getting to know you:
1. Why do you want the boss to know who you are?
2. What do you want the boss to know about you?
3. How can you present yourself in a way that will help you meet those goals?

Raising specific topics:
1. How does this help him/her? For example, does s/he just need to know as background, or is it possibly a way for them to reach a strategic goal they already have expressed? Do some homework to find out what the new boss wants to accomplish - talk to other people who have already had meetings, attend any public functions, read the announcement about their appointment, etc.

2. How could this help you? Think through what benefit you could get by raising the topic, as well as the potential consequences of not raising it. Also, make sure it won't hurt you to raise the topic at this point in time. Maybe you need to lay more groundwork or do some more homework.

3. What’s the desired outcome? The outcome can be simply for the meeting itself (e.g. now she knows I'm involved in this project) and longer-term (e.g. now this will become a priority for him, and resources will flow to it). Ask also what materials you need to bring with you or provide beforehand in order to better ensure your desired outcome.

4. What do you want the new boss to do, if anything? Clearly articulate exactly what you will ask, why they should say "yes," how you will ask it, and what you will do if they say "yes" - or "no." Think it through - what then will you need to do in response? What back-up materials must you develop and provide?

5. Are there any next steps after this meeting? For example, do you want to promise that you will do something? Do you want another meeting? Are there other people who need to be involved? What do you need to tell your boss?

In general, it's better to over-prepare for a meeting with a new boss than under-prepare. All that preparation will be put to good use sometime down the line, even if it's not used in the initial meeting. If nothing else, you'll feel more confident walking through the door for that initial meeting.