How often do you have conversations with your exec that lead to real results for both of you? If you’re struggling to level up your impact or take more initiative, the answer might be simpler than you think – start asking better questions.
Questions are a sign of leadership. Think about the best conversations you’ve ever had or the most interesting podcast interviews you’ve listened to. I bet they were full of good questions.
If you’re working with a new executive, ask more questions than feels comfortable.
Been with the same executive for years? You won’t need to ask as many – but never stop asking. You’re not perfect and you’re not your executive, so don’t be afraid to ask.
Here are six specific questions to get you started. Don’t ask all of these in one sitting. Spread them across a few one-on-one meetings. Arrive prepared with a suggested answer to each question in case your executive is stumped. Take notes, make an action plan, then revisit that plan in a few weeks.
- What’s one thing I could do to make your job less stressful this week?
Your job is to make your executive’s job easier so cut to the chase and ask this question. Be ready to propose an answer. It could be as simple as grabbing lunch for them when they don’t have time – or as complicated as formatting a 59-page presentation for the upcoming board meeting. Just don’t ask if you’re not willing to get your hands dirty.
- In what ways do I frustrate you? How would you recommend I change?
This gets the most cringes when I share it during training sessions. It’s certainly humbling and puts you in a vulnerable position but if your executive is frustrated about something you are or aren’t doing, you want to know. Frame it casually: “I’ve been working on my professional development and one thing I’m curious about is whether there’s something about the way I work that frustrates you. If so, I’d like to consider ways I can improve and be more helpful to you.” When I asked one of my executives this question, he said he wished I didn’t message him about minor details throughout the day. Instead, he suggested we go over small details once or twice a week to limit distractions. It was hard to hear at the time – but valuable. I’ve used this approach for years now and every executive loves it.
- What’s my greatest strength? Is it being used? If not, how could we get more out of me in this area?
You might be really good at writing communications to the entire company but does your executive give you the opportunity to do so? Or are they asking you to run pointless errands all the time? Ask this so you can start to work more from your strengths. And be ready to answer this one yourself to show you’re self-aware and ready for action.
- Is there a task or project you’re working on that I could take care of?
Don’t let your exec micromanage or work on tasks that aren’t in their job description. You might already have a list of tasks you can take off their plate – have this with you.
- Could we rearrange our calendars to make things easier, more enjoyable and more productive for you?
This answer should always be yes. Be aware of the meetings your executive should or shouldn’t be attending. Make it a priority to sit down with them and audit their calendar.
- How can I help you sort your to-do list?
Many executives know what they need to do but don’t know where to begin. You can help them break their to-do list into manageable tasks then work with them to sort the list so they don’t miss anything important.
Asking these questions takes courage and maturity, especially if your executive is resistant. But I’ve never regretted asking. I always take something away that helps me lead better – and often this sparks some of the best strategic business conversations we’ve had.
