Welcome to the Scarlet Ink newsletter. I’m Dave Anderson, an ex-Amazon Tech Director and GM. Each week I write a newsletter article on tech industry careers and tactical leadership advice.

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Hey there everyone! I had a few seemingly unrelated questions over the previous week, but I realized that my answers had a lot in common.

What I realized was that people were struggling to translate some need (a promotion, feedback, a big project) into an actionable request for their manager.

“I asked my manager for a big project I could lead, to make progress towards a promotion, and they said they’d try, but I’ve heard nothing for months.”

The core issue is that the request (“Let me lead a big project”) is expensive and complex and ambiguous.

Yes, sometimes people don’t want to help you. But often, the request you’ve made is much easier to just turn down. Or ignore.

What I wanted to talk about today was how to break down your needs into requests and paths to eventually get what you want.

Getting a mentor.

What do you get out of having a mentor? Usually two main things.

First, the obvious reason you get a mentor is for advice. You’re running into a personnel problem, or you want to be promoted, or you’re interested in learning more about a specific technology. Regardless, having an experienced person you can talk to regularly is helpful.

Second, the corporate reason. Assuming your mentor works at your company, it’s a great way to build a one-on-one connection with someone more senior than you. I repeatedly saw it being used (fairly obviously) to connect one growing leader with another more established leader. I know when I was heading towards Director, I ended up with a couple of regular VP mentors so that they’d know more about me.

As I grew in seniority at Amazon, I found there was an ever-increasing list of junior employees who wanted me to be their mentor. I couldn’t possibly say yes to many of them, because I was already fully booked with my real day job.

I ended up with a few regular mentees, and a few people I met with occasionally.

But how did those few people make it through my “I’m too busy!” filter?

Sometimes they were handed to me by someone important.

VP: “Hey Dave, this guy on my team needs a mentor. Can you do it?” - “Of course!”

But that clearly requires a senior person in your organization willing to speak up for you.

Other times they were someone I worked with regularly.

Junior manager: “Hey Dave, we worked on those two big projects together. Would you mind if we met occasionally, and I could bounce questions off you?”

But that requires an established relationship with your future mentor.

How can you build a mentorship relationship out of essentially nothing?

You make it extremely easy to say yes, and hard to say no. And I’ve seen a few people do that well.

“Hey Dave. I’m a engineering manager, and I was looking for someone to help me with two issues. One is a hiring issue, and I heard that you’re an experienced bar raiser. The other is a personal career question I had. Would it be possible to get 30 minutes of your time, so I could bounce those two things off you? If yes, I can look for an opening on your calendar and send an invite.”

That’s not perfect, but you get the point. Why is it easy to say yes, and harder to say no?

1. A general discussion can be exhausting (“Can you mentor me on my career?”) - because it is often up to the mentor to lead the conversation. This person has two clearly defined questions. Which means I can relax and just answer questions.

2. Many people default to an hour-long meeting. By making it 30 minutes, it feels like it’s a quick (and not costly) discussion. It’s a small ask.

3. They’ve done their homework enough that this is not a completely blind reach-out. They know I’m a bar raiser and have a tailored question for someone with my experience.

4. Not a huge deal, but by offering to do the next step, it becomes that much easier for me to say yes (and more awkward for me to say no).

So now we have a small, well-defined ask. They’re offering to do all the work. I just need to sit in my office for 30 minutes with them.

And what they’ve done is put their foot in the door. If that 30-minutes goes well, they totally have an opening for a follow-up meeting. I’m more likely to say yes to the next meeting, if I felt they respected my time, made the discussion feel productive, etc.

“Thanks for your time yesterday Dave! That was incredibly useful. Once I’ve tried your changes to our interview questions, would you mind if I scheduled a follow up 30 minutes? Perhaps 5-6 weeks from now?”

And so on. More than once I’ve been essentially sucked into a mentorship relationship because I was like a frog in a pot of water, being slowly boiled. Eventually you know the person well enough to just get a recurring meeting on their calendar...