Learning to Make the Ask

Getting better at negotiating, asking for help, and getting what we want. What's the worst thing that could happen?

Microsoft was the first company to say to me: we want you. They were the first offer out the gate during the fall of my junior year recruiting for full-time jobs.

I shared the news to my brother, who said: “Well of course they want you. Now, what are you going to ask for?”

I explained to him the facts at the time: I had no other offers and three other interviews cooking. Microsoft was the top company I wanted to work at, in the location I wanted to work for, and they had a pretty competitive package overall.

It would be unthinkable to show my lack of appreciation by asking for more. There also wasn’t anyone offering any more.

In response, he said, “Why not ask? What’s the worst thing that could happen? They’re not going to rescind the offer.”

After an inordinate time wordsmithing, I called Microsoft back and said: Thank you for the offer. I enjoyed meeting the team and I’m excited to work here. However, I would like to inform you that I’m expecting another offer soon, and I’m also with x, y, z other companies. I would be happy to stop all my interviews and accept immediately if you gave me a 10% increase in salary and a signing bonus. Otherwise, I am definitely interested and will keep you updated as I continue my process.

They called me back the next day and said yes. I signed.

What’s the worst thing that could happen?

This small negotiating success taught me a valuable lesson. I was scared and felt I had no leverage, yet I asked anyway. Because what is the worst thing that could happen?

Usually, the worst thing that could happen is they say no and I agree to the original arrangement. Comparatively, the upside is vast. They could say yes and I could get what I want.

If you’re reluctant to ask for things, like me, it’s possible that you too share a phobia of hearing the word no. It’s a pretty common thing.

On the other side of the desk, as a hiring manager, I have often seen candidates make a similar miscalculation. Most candidates don’t negotiate. What they don’t appreciate is that if they’ve made it through the full interview cycle to get an offer, the company is committed to them. The worst thing that would happen is that their ask is declined.

Asking takes effort and practice

The lesson from Microsoft applied beyond salary negotiation. I started asking for introductions, advice, information. It wasn’t natural at first, but I started gradually with low-stakes situations and built up over time.

Each time, I discovered the same thing: the downside was minimal and the upside was significant. But I still hesitated. Even knowing the odds, I’d find reasons not to ask.

Given the benefits of asking, why don’t we do it more? There are many reasons. In my case, I have a strong streak of independence where I like to do things for myself. Asking can feel like weakness, because it’s an admission I need help.

Objection: I don’t have anything to give in exchange

When I was early in my career, I rarely asked for help from more senior people because I felt like I didn’t have anything to give them in exchange.

On the other side, as a giver of advice, I realize now how rewarding it is to help someone. Altruism and connection is a strong motivator. If I could go back, I would have started asking sooner.

The way people “pay me back” is simple: they tell me what happened next. Something as simple as an email or text update saying how it turned out and their planned next move. The worst thing I could do is tell you I’m too busy to help. The best thing that could happen is we form a bond. This is how you cultivate successful mentorship.

Objection: Asking feels like imposing

I worried that asking for help meant imposing on others. Then I reflected that when people asked me for help, I didn’t feel imposed upon at all.

Think back to the last time someone asked you to do something, and how it made you feel. A friend asked me to review her marketing plan and I was happy to help. I felt recognized for my expertise and the ask was framed respectfully. I could decline if I needed to, but I felt good about sharing my thoughts.

Yet I realized I was holding a double standard. While I was happy to help her, I would be reluctant to make the same request because I was afraid to burden her with the request. The doubt was all in my head.

If you’re nervous about imposing, watch your phrasing. But don’t let that stop you from making the ask.

Objection: But what if they say no and I lose out?

Situationally, this objection can be absolutely valid. The advice is not to always ask, but to be more rational about what the loss scenario actually is.

I was approached to coach a founding team over several months in a series of in-person meetings. When I asked for a different structure, they decided to go another direction. I knew it was competitive, so asking risked losing the engagement entirely. It did. But I don’t regret asking because the original structure wouldn’t have worked for me anyway.

The point is that we often overestimate the downsides of asking, like if I hadn’t asked in my Microsoft story. The worst thing they could say is no and I’m back to accepting the original offer. But at least I asked.

Putting it into practice

Asking is a deeply underutilized muscle for many people, including me. We have a bias to only examine the choices presented to us instead of making new ones.

So how do you actually structure an ask?

Successful asks meet three criteria: they are specific, respectful, and win-win.

Specific asks provide enough context for the recipient to understand what you’re asking for and why they are uniquely suited for the task.

• Bad: Can I pick your brain over lunch?

• Good: I know you know subscriptions. Can I send over my metrics dashboard and our current roadmap and get your thoughts on how to improve?

Respectful asks take into account the time and effort it takes for the recipient to help. You modulate your request.

• Bad: Will you introduce me to the investors you know?

• Good: I’m fundraising and would love to get your feedback. Can I share the pitch and get your thoughts?

Win-Win situations are where you try to make it a net positive for both sides. If they’re helping, pay them back with feedback and updates.

• Bad: [crickets after a meeting]

• Good: So many helpful ideas after our meeting, thank you again. To follow up, here’s what I did and here’s how it turned out…

Learning to Make the Ask

In learning to make the ask, frequency is the key. Sometimes you’ll be successful, sometimes you won’t. We’ve got to learn how to manage our own psyche. If you make it a habit to ask for things, you’ll grow the skill and muscle over time.

Asking is often an avenue to helping others. I find being the first to ask often gives others permission to ask me in turn, which greases the wheels of connection.