You’re meeting your Grand-Boss (your boss’s boss), or maybe even someone higher up the food chain. How do you prepare for such an auspicious occasion?
Let me share how I approach this, including some dumb mistakes. The Big Boss meeting is a risky proposition, which can mean the difference between career advancement and stagnation. With these stakes, I am not leaving it to chance.
Whether you want to fly under the radar or take the fast track to Executive Island, you need to prepare yourself. The meeting will be won or lost before it even begins.
The keys to a great meeting:
- Don’t embarrass yourself or your chain-of-command
- Communicate new information in a positive way
- Learn broader context about the organization
- Follow up on everything
Let’s start by asking ourselves what precisely The Big Boss wants to get out of the meeting.
What Does The Big Boss Want?
The Big Boss is taking time out of their busy schedule to meet you for a reason. It might be a chore; HR told them that they needed to do them. Or maybe they heard what a bright shining star you are and want to shower you with money (unlikely). Perhaps they genuinely like meeting with people on the team, or maybe you have known each other for years. The context will help you prepare.
Consider what possible motivations they will have for the meeting. During the meeting, they might:
- Assess your performance.
- Listen for new information.
- Try to inspire or motivate you.
- Provide feedback (constructive or vague).
- Offer you something.
- Assign a new project.
Sometimes you are certain of the goal of the meeting because they told you. But even if you do, there will be hidden agendas and possible traps you can fall into that you didn’t expect. For example, they asked you to give status on a project, but you also receive critical feedback.
There may be a specific goal that you have no way of divining ahead of time. In this case, do the best you can in preparation by pondering their interests. And be ready for anything.
Some of My Embarrassing Mistakes
One time, I met my general manager and told her about another department I had been working with on the other side of the company. I thought I knew how she felt about that particular team, but I misunderstood the situation completely. After I complimented their skill and ability, her voice turned sing-song, and she said: “oh, that’s a fascinating perspective, I didn’t realize that.” I knew something was up. It turns out she was having some sort of political battle (the details I never found out) that I had stepped right into on the wrong side.
Another time, I was meeting a great-great-great-grand-boss after I had done pretty well on a high-visibility project in short order. As an ambitious young professional, I was certain I would instantly get a promotion in this meeting once I told him how I magically delivered. He gave me a nice compliment, one I still cherish, “my team was talking about [this problem] all the time, and now they don’t.” I thought this was an excellent opportunity to ask for more responsibility.
After the meeting, my direct manager called me into his office. He asked, “What the hell did you say in your meeting?” It may have been a stronger expletive. My innocent request to jump the chain of command had rolled back down.
Neither of these situations hurt my career too severely, but neither was optimal. But the lessons pushed me better maneuver the organization and seeing the reality that exists between the cracks of the org chart.
Can you get what you want from this meeting?
Perhaps you need a decision on a specific agenda item. Or you were summoned and aren’t sure why. Or maybe you have regular water cooler chats but want a serious conversation. Whatever your motivation, you should make sure you know what it is. It should be crystal clear in your mind.
Maybe you want to “make a good impression.” Being remembered positively is a noble goal, but a bit vague. Try to sharpen it. Perhaps, “Demonstrate that I am knowledgable enough to visit an important customer.”
If you know what you want to get, you will be able to strategize a path to getting it. And you must decide if this is the right forum to ask and if there is anything you can offer.
The View From Down Below
I don’t know anything about you or your company. But since you have a Big Boss, there is a hierarchy, and you’re not at the top. Perhaps you’re a middle-manager talking to another middle-manager. If you’re a founder or early employee, you will have to meet with investors and board members. Or maybe you’re a line employee talking to the CEO. In any case, we know there is a power and information disparity.
Don’t assume this means you are entirely at a disadvantage. While it’s true that the Big Boss may have more organizational Power (access to money, authority, hiring, firing, and the like), they are not as close to the action as you are. Depending on the depth of your organization, their level of indirection may be astronomical. While you may not see the forest as well as The Big Boss, you will have more granular details on the trees, branches, and leaves.
Sharing New Information in a Positive Way
Ask yourself this, what novel information can you provide about the day-to-day that would matter or change the perspective of those higher up? What data can you bring that would force the questioning of assumptions. Perhaps you know a project isn’t going as well as the reports claim. Ground truth about a shaky project is a dangerous piece of knowledge (see section on risks below), and therefore a treasured piece of information.
Try to see the organization from the top down. What recent news, trends, or competitors might be on the minds of those in charge. How do the needs of the company intersect with the specific domain or role of the Big Boss?
In addition to your deeper awareness of ground truth, try to take a step back and see how it fits into the bigger picture. What context might you be missing?
Seeking Greater Context
One common mistake I see when people meet Big Bosses is they want answers. They have burning questions about what’s going on. They want the green light. They have a particular situation and need advice. They want to know why we aren’t doing this-thing-that-I-believe-is-really-important.
By asking contextual questions and listening carefully, you can create an environment where the boss will comfortably share what matters and needs attention in the business. If you are looking for opportunities to grow, solve more considerable challenges, and matter more to the organization, this will lie in the context provided by the boss.
Some questions you might ask:
- “I saw that one of our competitors is doing X, what do you think that means for us?”
- “Based on our customer support data, I see a common request for X, is this something you consider to be in scope for our business?”
- “I’m curious how you see our company evolving in terms of X” (could be product lines, customer types, industry trend, etc.)
Note how these questions leave plenty of wiggle room, and they can share their thoughts without committing to an action plan. Craft open-ended questions with just enough specificity to start a conversation. Well-prepared, engaging questions require thoughtful research and signal attentiveness, poise, and capability.
What are the risks, and how will we mitigate them?
If you have a meeting of consequence, there will always be risks. Whether you like it or not, the world will be different when you walk out of that meeting (or more likely, close the zoom window).
As mentioned earlier, perhaps you want to share some information about a project that is going sideways. There is a clear risk that someone will look bad, and it will be your fault¹. Even if you save the company by raising the alarm, you will not be making any friends. And you may be seen as a gossip.
Talking about projects you’re working on or your accomplishments is generally OK, but consider the interpretation of what you’re saying. Be careful not to brag without sharing credit. Did you overstate the impact of the project? Does the big boss even care about the outcome?
The Follow Up
Make sure you follow up on anything you agreed to do. Debrief with yourself and write down what you think went well or could have gone better. Tell your direct boss (or co-founders) about the meeting and how you feel it went. If you weren’t able to take notes during the meeting, make sure to write down whatever action items you took (or think may have been mentally assigned to you).
Once I’ve completed 70% or more of these items, I will compose a short follow up email. I will cc my bosses up the chain to this person. I will thank them for the meeting. Short and sweet.
Now You’re Ready
You’ve thought about what your boss wants. You’ve done your homework. You know to steer away from touchy subjects. You have a few tasty morsels of information you can safely lob out. You’ve got a couple of great questions to gain a better context. And you know to follow up. At this point, you’ve done pretty much all you can. Just remember to stay present and on your toes and expect the unexpected.
There is no such thing as over-preparedness, only over-confidence.
 You might argue that it’s the fault of the person in charge of the project. But you will be responsible for sharing the bad news, so be wary.