7 Insider Tips for Hiring the Right C-Suite Advisor or Coach

How to get the most impact for your investment

Hiring a coach or advisor can be a major cost and commitment. How do you pick the best one for you? How do you make it a fantastic use of your time? As someone who has hired half a dozen personally and has been one for five years, I offer you lessons learned from my painful mistakes:

• How coaching failed me

• Advisors vs Coaches

• Three Biggest Issues with C-Suite Advisory

• Regularity and Duration

• Should You Hire a Board Member or Advisor?

• How to find an advisor

• Coaches are actually important too

How Coaching Failed Me

As the head of marketing at Atlassian in our pre-IPO hypergrowth, I felt very alone. We were using a new product-led growth model that was odd; I had challenges related to growth that made others tease me instead of help (“Wah wah,”) and at the time, I didn’t have experienced CMO friends or acquaintances. I turned to a coach who had business experience but at a very different scale company and not in marketing (she was the best HR had to offer). While discussing leadership skills and employee dynamics was sometimes helpful, it often felt like a waste of time. I remember her saying, “How does that make you feel?” With inner rage, I wanted to answer, “Like I want to talk to someone who knows how to do my job.” I needed more contextual help with the myriad of high-stakes, no-right-answer decisions that were pitting me against my first-time-founder CEOs. I needed someone who could help me organize my thoughts and approaches to get conviction on my strategy with insight into the actual work.

Advisors vs Coaches

I embarked on a journey over the next several years to find the coach I craved. I hired several, getting closer and closer to contextual; one was previously the owner of a marketing agency, and one was previously the CMO of a big public company. Their added context was much more helpful than the first coach, and they both gave me some great advice, challenging me and encouraging me. But both were still somewhat focused on more general topics because they couldn’t give me the exact tools, processes, and approaches that were specific to the stage of company, current marketing performance, and context of my exact business. I realized that, though I was looking for a coach, I really needed a business advisor.

Three Biggest Issues with C-Suite Advisory

Fast forward a few years, and I decided to become the person I needed but couldn’t find. I wanted to help CMOs and VPs of marketing feel more grounded, confident, and convicted as they faced tough odds in fast-paced, demanding roles. I focused primarily on where I had deep hands-on experience - in their context - advising CMOs or VPs of Marketing at hypergrowth B2B tech companies between $20 M - $500 M in revenue. I wanted to help them succeed without burning out as I had.

I started my business by advising CMOs and VPs exclusively. But I quickly realized three issues:

1. Many of the “marketing issues” weren’t actually marketing issues but were company strategy issues that showed up in marketing. Issues like targeting too many audiences at once, not having a differentiated enough product, or overhiring sales people ahead of demand required system-level change across product, engineering, and sales - they couldn’t be changed through the marketer alone.

2. Marketing leaders often didn’t have enough social capital to successfully argue this point without being perceived as defensive of their own “weakness.”

3. CEOs often didn’t tell the marketing leader what they really thought or needed on bigger themes because their conversations were focused on day-to-day issues. It was difficult, sometimes impossible, for the CMO to self-perceive all of the challenges they needed to address for maximum success.

Solution # 1: Cross-C-Suite Context

I realized that in order to make the CMOs successful, I also needed to be working with the CEO/President/COO - whoever was coalescing cross-departmental strategy. I need to be able to provide effective feedback that would reinforce the marketer’s effective process and plan (especially to CEOs who knew little about marketing and were unsure if they should trust their marketer). I needed to be able to discuss how the pipeline issue isn’t just a marketing problem and often help the company navigate the path forward. I needed to get direct, contextual feedback on the CMO to help them address unspoken concerns, navigate the complexity of their organization, and be seen as strong and effective. I needed to be able to understand the C-Suite dynamics that show up differently in a group than in 1:1 conversations. So I started adding CEO sessions alongside the CMO sessions and including attendance at one off-site with the executive team to observe, integrate, and support. These additions made my advisory of the CMO the rest of the year 10x more effective.

Solve 2: Trusted Network Endorsement

This kind of exposure and integration of the advisor is only possible if the advisor warrants this high bar of trust. CEOs are the recipients of tons of advice, which they need to sort through and take with many grains of salt. It has worked best to be able to “speak truth to power” and collaborate if I was recommended to the company by someone in the CEO’s most trusted network. Most of my most successful clients were introduced by one of their investors, board members, or C-Suite friends, which gave me the credibility to provide feedback on delicate situations and big strategy issues. Almost all of my clients have come through word-of-mouth direct referrals.

Solve #3: Relevant Experience

As I mentioned above, one of the most important aspects of success in my own experience was the relevancy of the advisor's experience. Like our dream employees, we want someone who has already seen the next several stages of growth at similar growth rates, selling to similar audiences, with similar go-to-market motions, in a similar or more advanced role. Thus I have focused in companies that already have product-market-fit, are scaling rapidly pre and post IPO, and are in the B2B space. I’m lucky to have both deep enterprise selling and product-led-growth experience, both technical and business-audience experience, giving me even more breadth.

I was so worried that my experience at Atlassian would continue to age (as some of it has), and initially didn’t realize how valuable my view into several companies at once would be for my clients. The fact that I’m advising 6-10 companies at any period of time gives me insight into the market dynamics, changes in performance benchmarks, prices for other marketing agencies or services, analyst insights, and more. While the nature of my job is supreme confidentiality, I can give market-trends from first-hand insight into the operations of other high-achieving companies. It’s critical to find advisors that have the relevant experiential context to make you successful.

Regularity and Duration

Several CEOs I’ve worked with have had many different advisors at the same time. Some of the advisors are very lightweight: “on call” whenever they are needed. But with the speed and complexity of a CEO’s life, they forget to engage them. I structure engagements with a lot more regularity - a CEO check-in every 2-3 weeks if we’re working closely, every month or quarter, and in some cases. A standing meeting ensures the advisor is providing value and continuing to build context to give better advice.

If the relationship is working, you often get more value from the advisor as time goes on. Many of my client relationships have been 2-3 years, continuing to renew. The early engagement includes more intensity, but the increased business and employee context over time is invaluable for providing better and more actionable guidance.

Should you Hire a Board Member or Advisor?

Many different early-stage founders consider adding a board member to get the guidance they need instead of an advisor. For instance, if a functional leader is weak, the CEO may hire an independent board member in that discipline. But there are risks that this short-term solution won’t maximize impact of that valuable seat. Financially, it’s a structure and recruiting mechanism that can help you hire top talent. But if it’s possible, engage an expert as an advisor first. You can benefit from their expertise on your short-term issue while getting better context on their long-term potential.

How to find an advisor

Many companies find advisors through their investors - access to amazing people-networks is one of the reasons boot-strapped Atlassian, and boot-strapped 1Password took on investors when they didn’t need money. Most investors have an operating partner who is a super-connector of talent, full-time and advisory. You can also find advisors through recommendations from CEO or CMO groups (Several of my clients have come from the amazing 10X CEO Group, the 6Sense CMO Coffee Talk or Empowered CMO groups). Reading experts’ blogs, hearing them speak at conferences, and reading books from experts you might want to hire are all possible paths to finding and evaluating an exceptional advisor as well.

Coaches are actually important too

After being down on coaching and fixated on business advisory, I’ve come full circle to appreciate both. I see the value of coaching more general leadership coaching for myself and others. While I work with my clients on CEO keynotes, fantastic marketing dashboards, crisis comms, board deck preparation, product launches, organizational design, and more … I also end up helping almost all my clients with leadership, organizational dynamics, inspiring themselves and others, employee issues, family and health balance and more. A C-Suite member’s life is an interconnected quilt of functional knowledge, interpersonal intelligence, and grit. If you can find a coach that can help with business advice, great! If you can find an advisor who can help with leadership coaching, great! Or maybe you need multiple different coaches for different aspects of your growth over time. I have…

P.S. You may also want a personal trainer to get in shape. But that’s a blog for another day.

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Carilu Dietrich is a former CMO, most notably the head of marketing that took Atlassian public. She currently advises CEOs and CMOs of high-growth tech companies. Carilu helps leaders operationalize the chaos of scale, see around corners, and improve marketing and company performance.

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