Help Your Boss Manage Your One-on-One Meetings If They Don’t Know What to Do

It’s reasonable to think that C-suite leaders would be well-practiced at conducting effective check-in meetings with their team members. But if that’s your assumption, you might be wrong. During a recent coaching session, a client expressed frustration that his C-level boss never articulates her expectations for his performance or even asks him about how — or whether — he’s making progress on his annual goals.?

Instead, the C-level leader is inclined to use one-on-ones to discuss current, short-term problems — almost as if my client’s check-ins are his boss’s opportunity to resolve some of her own work challenges, without actually providing any significant guidance or mentoring aside from tacit moral support. That makes it hard for my client to know where he stands, if his boss thinks he’s delivering results — or if, in fact, he’s wildly off course.

If your boss doesn’t know how to give you what you need or doesn’t know what you should need, then I recommend modeling how your boss can work with you rather than waiting for them to figure it out. Otherwise, you run the risk of never progressing as much in your career or reaching as much of your potential as you believe is possible.

Bring Along Your Own Agenda

I recommended to my client that he start managing an informal agenda for one-on-one meetings with his boss — always having three topic areas of discussion ready, whether or not he uses every topic every time. Bosses who want to discuss current problems may be perturbed if you appear to avoid the updates they crave, so be sure to provide some. But don’t let these updates take up more than a third of the meeting, and structure your discussion so that you can get something out of it too.

As part of your briefing on the timely issues you’re confronting, stick to just a few, explain what you and your team are doing about these tough situations, and ask, “What am I not seeing?” This question will create the opportunity for the boss to give guidance — not as criticism, but by providing their own perspective.?

You could even go a bit further and ask, “What else do I need to see from a company-wide or leadership perspective that would help my team do better in accomplishing our goals/serving the company?” This question gives you the opportunity to talk about your team’s work, opportunities, and goals — and verify that the leadership or company has not moved in a direction that would negate any of the good efforts your team is making.

Ask for Early Warnings

In the second part of your meeting — not every week, but perhaps every month or six weeks — be more explicit and ask your boss about their satisfaction with the progress of your team’s initiatives or your own personal goals. This showcases the progress you’ve made and solicits your boss’s feedback and support for continued or increasing accomplishment. It’s much better to give — and get — an early warning, so that it’s possible to correct course or ask for additional resources while there’s still time for repair.

Asking about your boss’s satisfaction can broaden their view beyond immediate problems to what’s going on with your group. It may also trigger their thoughts about how to strengthen initiatives or where you might sequence or prioritize efforts for maximum success — once again, showing you things you might not have been able to see or recognize on your own. As you hear about new aspects of the business, restate the lesson in it, so your boss knows that you are recognizing and learning this new thing.

It’s All About Expectations: Theirs and Yours

A third topic to raise, perhaps twice a quarter, is: “Do you have any new expectations of me? And how am I doing at meeting the old ones?” Leaders form new expectations of team members all the time. But if your boss is holding unstated expectations, it becomes difficult for them not to judge you for, say, lack of delivery, even if they never explained their expectations.

Asking these questions lets you learn whether your boss is forming new ideas about other things you should be doing or if there are other ways they would prefer you to deliver or behave. Sometimes these questions will even bring to the surface old expectations that you never even heard about.

Whatever your boss’s answers are, repeat back to them what you hear them say; then ask for the support you need to get those things done or to learn those behaviors: “Are you saying you’d like us to be more involved with the Schnickelfritz project? I can see how that would be good for A, B, C. Let me come back to you next time with some plans for how we could do that, because I think we may need additional staff/equipment/access/etc., to handle it successfully.” Or: “I’d like to work on that. Is there someone who can coach me on how to shift effectively from the way we’re doing it now to the new way?”

Whenever you’re not getting enough guidance from your boss, ask good leading questions — about how they would handle situations or how well you’re meeting expectations — to help you elicit opinions and advice that can help you satisfy their work goals and meet their expectations about how things should be done. And that will be good for you as well as for them.

Onward and upward —

LK

An earlier version of this post appeared on Workplace Wisdom.

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