jade rubick

How an executive advisor can help you grow faster and navigate unfamiliar terrain


When you’re navigating new territory, it is essential to have a guide. And if you want to grow your skills as rapidly as possible, it helps to learn from someone who has done it before.

Why use an executive advisor?

An advisor is someone who helps you produce better results with your work. They…

  • Suggest new ways to solve problems.
  • Help you navigate problems you haven’t dealt with before.
  • Point out mistakes you might be making.
  • Accelerate your career growth.
  • Provide new mental models for thinking about your work. Giving you more tools for your leadership toolkit.

How do executive advisors work?

Every advisor is different, so you should find out what approach a prospective advisor uses. I think my approach is fairly common, so let me share how it works with my practice:

With most of my clients, we conduct working sessions. They are one hour sessions, and are weekly, biweekly, or monthly. In these sessions, my client brings their current problems, and we problem-solve them together.

Each of us brings an essential part to the working session. I bring a lot of experience (both in terms of years doing this, and across many companies). I’ve seen it all before. My clients have their own experience and expertise. But most importantly, they have much better context on the problem and environment.

We talk through a few ways to solve each problem. And we review the tradeoffs of those approaches. I usually suggest solutions my clients wouldn’t consider. And I share tradeoffs they would miss. They in turn point out ways the environment may bias the solution in a particular direction.

As we work through these examples, we use them to clarify principles and mental models. That way, we are both solving an immediate problem, and building a muscle for addressing future problems.

Some of my clients use me to test their plans. They’ll share what they’re thinking, and have me walk through the tradeoffs, or suggest some alternatives they might not have thought of.

We walk out of these sessions with solid plans and new ways of addressing problems. It’s like pair programming, but for leadership!

Other advisors may have different styles or ways of operating, so be sure to inquire into their approach.

When to use an advisor

I see several profiles of leaders who reach out for advisory help:

Leaders who are in new territory. Typically leaders approach me when they’re getting in a little over their heads, or their current approaches seem to break down. (This often happens at ~20 engineers or ~50 engineers in an organization). Symptoms are too many direct reports, too much relying on them, engineering velocity slowing down, or quality problems emerging.

Leaders who are promising but need support. Often very talented leaders who have a little less years of experience seek out advisors to make sure they’re well supported. Sometimes their boss may even insist on it. This can help bright and capable leaders step into situations that may otherwise feel risky for the company. (Hint: you can use that to your advantage to get companies to take a risk on you by pairing the responsibility with an advisor)

Leaders who are growth minded and want to be as effective as possible. These leaders are aware that their growth is magnified if they get good feedback on their work. So they seek to accelerate their growth by choosing an advisor who will give them new perspectives.

Leaders who are part of a work culture that encourages growing their leadership. Some companies invest in their leaders, because they view it as a high leverage place to invest. Making a leader 10% better has a greater than 10% impact on their area of the company. In these companies, most of the senior leaders have executive advisors or coaches.

How to choose an advisor

I recommend you interview a couple of advisors to determine which person is best for you. Ask people in your network for recommendations. Select a few, and contact them.

With my potential clients, I like to do a practice session. This gives the potential client a feeling of what it’s like to work together. Ideally they will do the same practice session with a couple of advisors, and see what kind of insight they get from each person. And they should also evaluate how comfortable they feel being vulnerable or showing their weak areas with the advisor.

Do keep in mind that sessions will get better over time, as you develop a working relationship together. But the sample session will give you an idea of what it’s like to work with the person. So I recommend asking for a sample session.

What to look for

What should you look for in an advisor?

  • Someone who has been through the stages you’re going through.
  • Someone you communicate well with.
  • Someone you can be vulnerable with.
  • Someone who listens as much as they speak.
  • Someone who doesn’t have the same solution to every situation.

The last one is something I think it’s important to emphasize. How flexible is the advisor’s thinking? Do they respond to every situation with the same solution? That’s often a red flag.

The problem with determining the effectiveness of an advisor is that many people will confidently give you bullshit suggestions that can actually make your life worse. As humans, we often conflate confidence with competence. What I would look for is the level of insight they give you. And compare it with what others give you when given the same information. Another suggestion is to ask them about their thought process and why they are making that recommendation.

Rates for advisors

Rates vary greatly depending on the advisor. I’ve seen rates that vary by an order of magnitude! If you’re on a budget, you can probably find someone fairly inexpensive.

But you have to be careful with your choices. You’re hiring someone for their expertise, not just for them to coach you (more on the difference between coaches and advisors later).

Ideally, your company should be paying for the advisor. What I tell companies is to use this heuristic to determine whether the rates are reasonable for an advisor:

If you took the yearly cost of the executive advisor, and compared it to how much it would cost to hire an additional engineer, how does it compare? Compare both the anticipated impact of the advisor, and the cost. When you consider the impact on the company, it’s generally a very smart investment, even if it looks quite expensive. A good advisor can help you avoid expensive mistakes, and improve the trajectory for an entire department. That’s often worth it even if it’s quite expensive.

Advisors can be expensive, and even feel out of reach for individuals. Why? Consider the economics of the situation. A highly experienced engineering leader can command a salary of $300-500k/year, plus 0.5-2% of the equity of a company, and bonuses. Total comp can be $350-$1MM a year.

Advisors also have a lot of overhead to just be an advisor. To give you an idea from my own consulting: I have 4 or 5 hours of meetings with prospective clients for every client that signs up (and I think that’s a good ratio). I need to have about four hours of meetings a month just to be sustainable as a business, and it fluctuates greatly. I have to manage taxes, health insurance, and deal with unpaid vacation. When you add all these things up, the rates can end up being higher than you might expect.

I personally provide a 50% discount for individuals, because otherwise many of them can’t afford it. And many of them find even the discounted rate out of their reach. (This is why I started offering group leadership coaching.)

If possible, go through your company. An easy way to ask about this is to ask if they offer executive coaches or executive advisors. If they don’t, ask if they’d be open to it. Many leaders don’t want to seem “weak” by asking for this. You would be surprised how common executive advisors are. Many companies do offer this kind of investment in their employees, or are willing to. You may be surprised that the person you’re asking already uses an advisor!

Most advisors charge either hourly, or by the number of meetings. My own rates are monthly charges, based on the frequency we plan to meet. That seems to be pretty common.

What about using an executive coach?

Here’s what ChatGPT says is the difference between using a coach and an advisor. I have to admit it’s a good summary of the difference.

“Both advisors and coaches can provide guidance and support, but there are some key differences between the two roles.

An advisor typically has specialized knowledge or expertise in a particular area and offers advice based on that expertise. They may provide recommendations, opinions, or solutions based on their experience and knowledge to help a person make informed decisions.

On the other hand, a coach is more focused on helping a person achieve their goals and develop their skills or abilities. Coaches typically ask questions and use various techniques to help their clients identify their own strengths and weaknesses and work towards self-improvement. Coaches may also help their clients create action plans and hold them accountable for their progress.

Another key difference is that advisors tend to have a more directive approach, while coaches are more non-directive. Advisors often offer specific recommendations and may even make decisions for their clients, while coaches help their clients find their own solutions and strategies.

Overall, both advisors and coaches can be valuable resources for people seeking guidance and support, but they have different areas of focus and approaches.”

You’ll find that there is a continuum between the two. Most advisors also do some coaching. Some coaches also do some advising. I do both.

My advice for engineering leaders is to find someone who leans towards advising. The reason for that is that having deep experience in engineering leadership is something that is worth a lot. There is a wide body of knowledge and expertise that you will be able to tap into from advisors that understand that domain well.

But this does depend on the goals you have in mind. If you’re looking to be a more effective communicator, a coaching approach may be more appropriate. And if you’re wanting to have more perspective as a leader, a coach may be more appropriate.

Both are reasonable options. I would look at this as a spectrum that you can use to evaluate people you’re considering.

Any questions?

Let me know if you’re looking for advisory help. I both do this myself, and also maintain an online community of people doing similar work.

Also, if this article didn’t address something you think it should, I’d love to hear your feedback!

Image by Simon from Pixabay

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