Questions to Ask When Networking with Senior Leaders
Questions for the short conversations you get with executives and other senior people: at a conference, after a town hall, or in a twenty minute introduction. Written for people several levels below the person they are talking to.
The questions
Open any question for the note
What are you spending most of your time on this quarter?
Why ask it
Better than asking what they do, because it gets a current and concrete answer instead of a job description. What a senior person is personally spending time on is usually the thing that is not going smoothly, which is the most interesting part of their week.
What made you come to this particular event?
Why ask it
A low-cost opener that gives you something real to work with: they are recruiting, they are looking at a market, they were asked to speak and would rather be elsewhere. It also signals you have noticed they had a choice, rather than treating them as furniture.
What has changed most about the business since you took this role?
Why ask it
Invites them to compare then and now, which surfaces the shifts they think matter rather than the ones in the press release. Vague answers here often mean they inherited a strategy they have not yet made their own.
Which part of the strategy is hardest to explain to people outside the company?
Why ask it
This finds the pressure point. The part that is hard to explain is usually either genuinely novel or not fully worked out, and either answer teaches you more than a summary of the plan would.
When you look at a team, what tells you it is working before the numbers do?
Why ask it
Experienced leaders have specific tells: how fast bad news reaches them, whether people disagree in meetings, who answers when they ask a question. A leader with no answer beyond engagement scores is probably managing by dashboard.
What kind of problem do you wish people would bring you earlier?
Why ask it
Practical intelligence you can use the next day, and it tells you what they consider their job. It also gently reveals whether their organization currently escalates things to them too late, too often, or not at all.
What do people at my level tend to misunderstand about how decisions actually get made?
Why ask it
Senior people usually enjoy this because the misunderstanding frustrates them too. Expect answers about timing, about how many people have to be aligned, and about how often a decision was made weeks before it was announced.
Which skill got you promoted, and which one stopped being useful?
Why ask it
The second half is where the value is. Nearly every senior person had to abandon the thing they were best at, and hearing which one and when gives you a map of what to hold on to and what to let go of.
How do you decide what to say no to?
Why ask it
At their level the constraint is attention, not effort, so this is the question that gets at their real operating method. Watch whether they describe a system or just say they are bad at it, which is a more honest and more common answer.
Where do you get information you trust, given how much is filtered before it reaches you?
Why ask it
Everyone senior knows they are managed by the people who report to them, and few are asked about it. The answer names the specific people and channels they rely on, which tells you how information really travels in their organization.
What is the part of this job you did not expect?
Why ask it
Almost always the volume of internal politics, the loneliness, or how much of the week is spent on communication rather than decisions. It is a human question that does not require them to perform, which is why it usually lands well.
What is a decision you made this year that you would make differently now?
Why ask it
Only ask once the conversation has warmed up. A leader who can answer plainly, without hedging into a lesson-learned anecdote, is one worth staying in touch with, and the answer shows you their actual standard for judgment.
What advice were you given early on that turned out to be wrong for you?
Why ask it
Easier to answer honestly than asking for their best advice, which produces a stock reply. It also spares you from following career guidance that only worked in a different era or a different industry.
Who shaped how you lead, and what specifically did you take from them?
Why ask it
The word specifically is what stops this becoming a tribute. Look for a concrete practice rather than an adjective, because the practice is something you can copy and the adjective is not.
Where do you think our industry is being changed in a way people are not taking seriously yet?
Why ask it
Invites a real opinion rather than a trend list, and their answer tells you what they are quietly betting on. If the reply is whatever is currently in every keynote, you have learned they are not thinking ahead of the room.
What do you look for in someone you would actively sponsor, rather than just mentor?
Why ask it
Sponsorship means spending their own credibility on you, and the bar is different from mentoring. Their answer is the closest thing you will get to the criteria used in rooms you are not in.
What would you want to be true about this organization in three years?
Why ask it
Pulls out the version of the future they would be proud of, which is often more candid than the official plan. Note whether the answer is about the business or about the people in it.
If you were at my stage now, what would you spend the next year getting good at?
Why ask it
Puts the question in their frame of reference rather than asking them to plan your career, so the answer stays useful even if they barely know you. Be ready for advice that reflects their path more than the current market.
Is there someone you think I should be talking to?
Why ask it
The most valuable ask you can make, and the least demanding, because it costs them a name rather than their time. If they offer one, ask whether you may mention their name when you reach out.
Would it be useful if I sent you anything, or is there something I can be helpful with?
Why ask it
Ends the conversation as an exchange rather than an extraction, and it is genuine: junior people often have information senior people lack about how something is landing on the ground. Keep the offer small and specific so it is easy to accept.
Making a short conversation count
Practical guidance for the conversation itself
How to handle the encounter
Do the reading, then do not perform it
Know their role, recent announcements and anything they have written. Use it to skip past the basics rather than to demonstrate that you looked, which reads as flattery and burns the little time you have.
Plan for four minutes, not forty
Most of these conversations are short and get interrupted. Pick two questions you actually want answered and lead with the better one, rather than working through a list you will never finish.
Ask one question and then stop talking
The most common failure is filling their pause with your own view. Senior people are used to being talked at, and someone who lets a silence sit is unusual enough to be memorable.
Follow up in two sentences, within a day
Reference one specific thing they said, say what you did with it, and ask nothing. That single message is what turns a conversation into a contact, and almost nobody sends it.
Picking questions for the setting
Two minutes at a conference or after a talk
- 1What made you come to this particular event?
- 2What are you spending most of your time on this quarter?
- 3Where do you think our industry is being changed in a way people are not taking seriously yet?
A scheduled introduction inside your own company
- 1What kind of problem do you wish people would bring you earlier?
- 2What do people at my level tend to misunderstand about how decisions actually get made?
- 3What would you want to be true about this organization in three years?
- 4Would it be useful if I sent you anything, or is there something I can be helpful with?
A second or third conversation, once they know you
- 1Which skill got you promoted, and which one stopped being useful?
- 2What is a decision you made this year that you would make differently now?
- 3What do you look for in someone you would actively sponsor, rather than just mentor?
- 4Is there someone you think I should be talking to?
What goes wrong
Asking for a job in the first conversation
It converts a person who was curious about you into a person managing a request. If you want a role, build two or three exchanges first and then ask them who to speak to rather than asking them to hire you.
Asking something their annual report answers
Questions about headcount, revenue or published strategy signal you did not prepare and waste the only window you get. Use public information as the starting point, not the topic.
Pitching your work when they ask about you
When they turn the question round, give a short, plain answer, twenty seconds, and hand the conversation back. A rehearsed pitch makes the exchange feel transactional and ends it early.
Treating access as the goal
A photograph with an executive and no follow-up is worth nothing. One person who remembers a specific thing you said beats ten introductions you never build on.