One of my friends recently landed a new senior management job. We got together over coffee one weekend to brainstorm what he should do to start strong in his new role. This post is a sanitized summary of our discussion. I hope you’ll find ideas in this post that you can pick up and apply immediately.
Ask these questions at your first 1:1 meeting
The most important meeting in your first week at a new management job is a 1:1 conversation with your new boss. Reserve at least 45 minutes, preferably an hour, for this first meeting. The objective is for you and your boss to create a shared understanding of what’s expected of you.
The simplest way to understand your boss’ expectations is to ask good questions. Here’s a list to get you started.
1. How will my performance in this role be measured?
In the best-case scenario, what would I have accomplished in the first 30 days, first 90 days, first 180 days?
- If your boss can give you specific answers for each of these timeframes, then you’re in luck. They know exactly what they hired you for, and they have no trouble telling you exactly what they want. If they’re the organized sort, they may even have these expectations written down in an onboarding document. Your conversation in this first meeting becomes a straightforward overview of your onboarding plan.
- If your boss only has vague answers for you, take heart, because you now have a golden opportunity to define your role. Your best bet for dealing with vague expectations is to: (a) get a high-level brain dump from your boss, (b) schedule a check-in meeting two weeks down the road, (c) spend your first two weeks gathering as much information as possible, and (d) write up your own ‘Objectives and Plans’ for the 30-day, 90-day, 180-day periods based on the information you gathered.
2. Which items on this list of expectations are critical?
What’s mandatory or high priority? Which items on this list are nice-to-have?
Once you have the list of expectations (whether these are given to you or proposed by you), your next step is to confirm what’s essential and what’s not. This question is worth asking because the things that are at the top of your boss’ mind are likely to be the urgent things, and not necessarily the important things . . . and you want to focus on the important things.
Try to frame the conversation along these lines:
“Based on (our conversation / my data gathering), here are the objectives that I believe are the most critical for me to accomplish, listed in order of priority. In an ideal world, I will have achieved every objective on this list by the corresponding date noted. Realistically speaking, however, we know that I’ll need time to get up to speed and will likely encounter blockers. So I propose to set a target to complete the first X items on the list by the dates listed. If I do that, then I will have met your expectations and performed my job well. If I do more than that, then I’ll have exceeded your expectations. Does that sound right to you?”
You’ll both talk through the items listed until you agree on prioritization and timeframes. Use this time to clarify the scope and “success criteria” for each objective.
3. Who should I meet in my first 30 / 60 / 90 days and what should I know about each person or team?
What are the political minefields I should watch out for with each? Who are the key people behind the scenes? Who are the stakeholders that we need to keep in the loop and happy with our work? What are their concerns?
Once you have the list of people and teams to meet, ask who you should be sure to meet first to work on your highest priority objectives. Also, ask if it’s possible for your boss to send an intro email to the people on your list to let them know you’ll be reaching out to sync with them. Offer to draft the email for your boss so you can include pertinent info about your background and all s/he will have to do is send the email.
4. What documentation should I read to succeed in my role?
Note: You should also ask this question of each team and person you meet.
Keep a list of everything that people mention and aim to get access to it within days of learning that it exists. Then use the list of objectives and people (from the three steps above) to figure out which things you need to read first.
As you get settled in, keep a list of documentation, policies, procedures, standards, templates, etc. that you think should exist but have not yet found. You can ask the people you meet if they’re aware of such information and with luck, they can tell you where to find them.
5. What things keep you up at night that you hope I can help with?
What are our top risks? Are there fires that I should start actively fighting?
These questions are a roundabout way of restating the first two questions, and they give your boss an opportunity to open up about their concerns. It gives you one more way to confirm that there are no expectations still left unsaid.
This type of question also helps to ‘prime’ your boss into thinking of you as a potential problem-solver. But be careful: this question can spawn new items for your list of priorities. Resist the urge to take these things on without first removing another item that’s of lower priority.
6. If you have a chance to re-do some things in the past 12 months, what would be the top 3 do-overs in your wishlist and why?
Your boss’ response to this question will highlight areas where there are potential risks, interpersonal tensions, or political roadblocks.
It’s always worth asking this type of question because (a) you can get a sense of how much your boss reflects on the consequences of their actions, (b) you can avoid repeating your boss’ mistakes, and (c) you can be the “good cop” on your team that helps smooth things over with other teams.
Schedule a Regular Check-in Meeting
No matter how thorough you both are on your first meeting, it’s inevitable that you and your boss will need to update your list of objectives. You’ll want to update your list because you’ll have more information and context. Your boss will want to update your list because priorities and circumstances evolve. So before you leave your first 1:1 meeting, agree on a regular cadence for check-in meetings with your boss, where you can use that time to jointly update your list of objectives.
Have a clear idea of what objectives you will have achieved before that next meeting. You don’t want to come back with everything still “in progress” and have nothing tangible and valuable to show.
Write everything down
If an onboarding document was not created for you, make one for yourself. Write everything down and annotate the document with copious notes as you meet people and gain insight into the specifics of your role, your boss’ priorities, and the company’s strategy as a whole.
Since you have a management job, you’ll be expected at some point in the future to ease new hires onto your team. When that time comes, use the same questions above — this time from the perspective of the person answering the questions — to fill in the details of your new hire’s onboarding document. You’ll have a much easier time preparing that document if you can refer to an extensive set of notes.
I hope these ideas help. Good luck!
