Why High Performers Need Mentors More as Their Careers Advance

Welcome to my newsletter! I'm Dave Anderson, an ex-Amazon Tech Director and GM. I write this newsletter I've called Scarlet Ink, which is a weekly newsletter on tech industry careers and tactical leadership advice.

Free members can read some amount of each article, while paid members can read the full article. For some, part of the article is plenty! But if you'd like to read more, I'd love you to consider becoming a paid member. 99% of my articles are intended to be evergreen (readable and valid forever). Some weeks I have fresh content; other weeks I'll update/rewrite something from 4+ years ago because I want to keep the quality of all articles high.

I sat in my office, an expectant look on my mentee's face. As we sat there, without either of us talking. I felt awkward, annoyed with myself, and frustrated with my mentee.

One of the core aspects of being a relatively senior leader at a company like Amazon is that you multitask. A lot. And the way I've maintained productivity while working on far too many disparate things, is that when possible, I try to get tasks off my plate quickly.

For example, while sitting in my office working on seven different things, one of my engineers sticks their head in and asks if I mind if they redesign one of our internal admin tools.

There is a brief moment where I wonder what was wrong with the old one, and if our internal customers complained, and if the design team is involved, and if we'll warn people before the UI changes, and if the features are being changed at all with the UI, and if that engineer couldn't possibly do something better with their time.

But I say, "Sure, go for it", and go back to my other work. Because they're a smart engineer, and the downside is low. And occasionally we'll end up with a freaky animated drag-and-drop interface that our lead designer absolutely hates. Whoops.

So in a similar vein, this Amazon employee asked me a few weeks ago if I could be their mentor. I was probably doing three other important things at the time. Instead of asking questions and preparing them with my expectations for mentees, I said, "Sure, grab time on my calendar." Again, whoops.

Therefore, the first mentor action I took was to explain to my mentee that you usually come to a mentorship meeting with an agenda of things you'd like to discuss. You don't walk into my office, sit in a chair, and then smile expectantly at the mentor, expecting them to figure everything out.

As a side note, before we get too far into this, I'll probably be referring to coaches and mentors interchangeably. I generally view a mentor as a non-paid volunteer position and a coach as a paid position. Although they tend to perform the same general service.

Why should YOU get a mentor?

Many people are reluctant to get a mentor. I've declined the opportunity more than once myself earlier in my career.

I remember repeatedly offering promising employees to find them a mentor within Amazon, and they regularly turned me down. Or gave me the equivalent of a vaporware "maybe!" which they had zero intention of following up on.

Why are so many people reluctant to use a mentor? I think the clue is in the most common phrasing of the rejection.

"I think I've got this. I'll let you know if I need help."

People mistakenly see getting a mentor as admitting that they have a problem. One small reason might be that when someone is underperforming, we frequently call that period right before they're fired, "putting them into coaching."

Which is absolutely unrelated to mentors and paid coaches and the act of being coached. It's just corporate speak for, "We're going to pretend the manager is coaching them for improvement while simultaneously documenting their continual failures so that we won't get sued when we fire them."

I'd argue that mentorship and coaching are best suited for top performers. The relationship is about improving the performance of an employee, and investing that expensive time of two employees is only worthwhile if the employee has a significant amount of growth potential. This means the employee needs to be self-driven and have an upward trajectory. Those aren't the traits of an underperformer.

Seth Godin wrote an article on this topic, in which he explained that in most fields, having a coach is expected for high performers. But weirdly, many corporate employees shy away from the concept.

The need to have a mentor or coach only increases as you gain experience. As a new college hire, the mistakes you'll make are obvious. It's easy for any co-worker to point out better ways to accomplish your job. The challenges you'll encounter will be straightforward. Improvement comes naturally, as long as you're paying attention at all.

As you grow in experience, the mistakes you'll make and the challenges you'll encounter will become more ambiguous and complex. Employees who are open to growth and development will often find a wealth of learning from working with another experienced leader. Or from reading a newsletter. Whatever floats your boat.

Mentorship and toolboxes.

As I said, I also rejected the idea of a mentor earlier in my career. Not just because of my above concern (admitting weakness). I just figured that a mentor would tell me that I should do A or B, and I already knew that A or B were options, and I didn't want or need someone telling me what to do. I emotionally reject the idea of someone telling me how to do something.

The thing is that a good mentorship relationship isn't about telling you which option to do. It's more typically about offering a way of thinking or looking at a problem that you hadn't considered.

I love the concept of a mental toolbox. Your mental toolbox is your skills and knowledge you reach for when you encounter a specific problem or opportunity at work.

When you begin your career, you have a relatively empty toolbox. Conceptually, you have a hammer and some nails. You default to treating most issues the same way because you haven't done much.

I remember interviewing an engineer, and I asked him how he'd deal with a project that had a deadline he was likely to miss.

"I'd work longer hours."

I nodded. "Ok, but the due date is approaching and it looks like you're going to miss it. What else can you do?"

"Um. I'd work even more hours. I can work really hard when I need to."

An engineer with a reasonably sized toolbox would recognize that you can also try to change the due date, ask for more resources, simplify the project requirements, etc.

Through the school of hard knocks and observing others, you slowly put more tools in your toolbox. You begin to recognize patterns in the challenges and situations you encounter, and you can recognize that a specific tool you have used in the past could work for this situation.

"Oh, our on-call is occasionally getting swamped? In the past I've seen a secondary on-call work well."

Your mental toolbox grows automatically with time and experience. But how can you more quickly augment your toolbox? A mentor is a great option.

Because a mentorship relationship isn't necessarily about talking to someone with more experience or better skills (although that's nice). The key ingredient is that it's someone with a different toolbox. And they're willing to share their tools with you. Which sounds like an HR violation, but I totally don't mean it that way.

If you're in a challenging position at work, you regularly encounter situations where you need to decide your course of action, and you're not positive that you're doing the right thing. Importantly, you don't know what you don't know. You don't realize there are other options you're not considering.

When I moved from a Technology Director at Amazon to a General Manager (essentially a move from a tech leader to a business owner), this was a large official step into product management. Due to how Amazon operates, I'd certainly done some product management tasks in the past, but I'd never been responsible for the whole shebang.

I asked two product management leaders I respected to mentor me through this personal growth. Not because I thought they were better than me, but because their toolboxes had different tools in them. They had various product management experiences that were foreign to me. I wanted to understand their tools.