How to get a senior leader to back you

 
Many years ago, I was making tea in our office kitchen, when the CTO walked in.

I had been curious about her journey since a while. How did she get to where she is, and make the jump? And could she help me get there too?

I said hello. She smiled and said hello back. I made some comment about how the kettle always takes forever. She agreed, made her tea, and left.

I was so annoyed at myself afterwards. I’d used my 90 seconds with someone who could change my career to complain about a kettle.

Here’s what I didn’t see at the time: one chance meeting was anyhow never going to have the effect I wanted it to have.

Why one perfect chat won’t change your career

When we think about getting close to a senior leader, and potentially be sponsored by them in future, most of us imagine a perfect conversation. Where we say the right thing, leave a strong impression, and walk away as “someone they remember.”

That’s not how it works.

Think about what a sponsor does. A sponsor is someone who puts your name forward when you’re not in the room. I wrote about this in the linked article here.

Sponsoring someone is a big action for a senior leader - their own reputation is on the line. They recommend you for stretch roles and back your promotion when it comes up.

Would they do that for someone after a 90-second chat in the kitchen?

A senior leader needs to see you over time before they’ll back you publicly. They need evidence: how you take advice, how you handle challenges and setbacks, what results you deliver. That trust takes repeated exposure to build.

So you need a way to get back in front of them, again and again, without it being weird.

The unlock: asking for career advice
 

Couple of years after the CTO meeting, in a new company, I tried something different. Our CEO was a guy, the founder of the business, and I was determined not to waste my chance again.

I asked him for a 20-minute chat - I framed it as wanting his perspective on something specific I was working through in my career. He agreed.

Then I followed up with my actions, and a follow up 20-minute chat.

By the end of couple months, he knew my name, my work, and what I wanted next. When the maternity cover for our Chief of Staff role opened, he was the one who put my name forward.

What worked with him: asking for career advice.

Why “any advice for me?” doesn’t work

The default move is to ask a senior person “do you have any advice for me?” or “any tips for someone earlier in their career?”

It sounds reasonable but almost never lands well. The senior person doesn’t know you yet, so they have no idea what you actually need. They fall back on generic tips: work hard, be visible, network. You nod, thank them, and the conversation dries up.

You walk away with nothing useful, and they forget you within a week.

The fix is to ask about something specific they’ve actually been through themselves. When you do that, they draw on a real memory of their own experience instead of inventing advice on the spot. The whole conversation feels more honest, and you walk away with something concrete to act on.

Here are the three topics that worked best for me.

Topic #1: confidence and imposter syndrome

Every senior leader I’ve ever spoken to has felt like an imposter at some point. Most have never been asked about it directly.

The first time I sat down with my CEO, I told him I sometimes felt I didn’t belong in senior meetings. I asked how he’d handled that feeling as a first-time founder, sitting across from investors who’d have decades of experience.

He told me indeed he didn’t know whether he is doing all that’s expected of him as a CEO, now the company was scaling fast. He also told me about the books he was reading on the subject - and we exchanged our reading lists.

That story changed how I saw him. And it changed how he saw me, because I’d shown him I was someone who thinks about confidence honestly and curiously, instead of pretending.

Try this: “Hi [name], I’ve been reflecting a lot about confidence and imposter at senior levels and would really value your perspective. Was there a moment in your career when it shifted for you? Would you have 20 minutes in the next couple of weeks?”

Topic #2: what they look for in a leader
 

By the second conversation, I’d been preparing for my annual review and was thinking about the level above. So I asked my CEO directly: what did he actually look for when he decided someone was ready to step up?

He told me about three people he’d promoted in the past two years and what was the biggest factor for each of them.

What makes this topic work is that you’re getting the senior person to name skills and traits they often haven’t put into words before. Once they’ve said something out loud to you, they start associating it with you.

Try this: “Hi [name], I’ve been thinking about what makes someone ready for the next level. I’d love your perspective on what you actually look for in a leader you’d promote. Would you have 20 minutes again in the next couple of weeks?”

Topic #3: their own journey
 

This one is for when the relationship has deepened a bit. You’ve already had a couple of conversations, and they know you take their advice seriously.

For the third conversation with my CEO, I asked about his journey as a founder, how it felt like in early years.

There’s a piece of research from Harvard showing that talking about ourselves activates the same brain regions as money and food. People love being asked about their story, especially the parts they don’t usually get to share. By giving him the space to tell his real story, it created an even deeper connection.

Try this: “Hi [name], the last few conversations have meant a lot to me. I’d love to hear more about your own journey. Would you have 20 minutes again in the next couple of weeks?”

The bit most people skip

Between every conversation, send them one short email, to tell them what you did with their advice and what happened.

Not “thank you so much for your time.” Something like:

“After our chat I tried [the thing they suggested] in my next leadership meeting. The team responded by [what happened]. I’m thinking about it now as [your takeaway].”

That email is building the relationship. It tells them you listen and take action, and you’re worth backing.