Name: JD Miller

Title: Operating Advisor

Organisation: Five Arrows Capital Partners

JD Miller, PhD, is a seasoned executive leader specializing in sales transformations for PE-backed and pre-IPO firms.

With six exits and decades of experience in multinational tech companies, he excels in building high-performing teams and implementing rapid growth strategies, and shares them in his bestselling book, The CRO's Guide to Winning in Private Equity. As an Operating Advisor for Five Arrows Capital Partners, JD leverages his expertise at the intersection of business, technology, and humanity to strengthen the companies he works with.

A prolific author and conference speaker, he serves on multiple boards and actively supports philanthropic causes. JD's work in empowering underserved communities earned him recognition as one of Chicago's Most Inspiring individuals, while his professional work earned him the recognition of “CRO of 2024” by Sales Enablement Collective.

More at www.jdmillerphd.com

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

We’ve gone through the interviews and asked the best of the best to come back and answer 7 MORE Questions on Leadership.

I hope JD's answers will encourage you in your leadership journey. Enjoy!

Cheers,

Jonno White

1. As a leader, how do you build trust with employees, customers and other stakeholders?

I build trust by prioritizing transparent communication, a focus on outcomes, and mutual respect. This means actively listening to concerns, being honest about challenges, and following through on commitments.

In practice, this translates to:

For employees, I make sure that everyone understands their role in our shared success and that they have the tools and support necessary to do their jobs well. I am also a huge advocate for talent development, and I work to create a culture where everyone is continually growing their skills.

For customers: I view every customer as a long-term partner, and my teams work to understand their needs and tailor solutions accordingly. When things go wrong (which they inevitably will!), we are honest about what happened and do our best to make it right.

For board members, I communicate honestly and frequently about our performance against the plan. When we are at risk of missing targets, I proactively explain what is going wrong and what we are doing to fix it.

Ultimately, my goal is to create a culture where everyone feels valued, respected, and empowered to achieve their best. When we all work together, honestly and collaboratively, I believe that we can achieve phenomenal things.

2. What do 'VISION' and 'MISSION' mean to you? And what does it actually look like to use them in real-world business?

Mission and vision are two distinct concepts, both of which are critical to the success of a business.

Mission is the fundamental purpose of the business. It is the north star that guides every decision, and it is why the organization exists.

Vision is how the business will achieve its mission. It is the day-to-day work that everyone does to move toward the fundamental purpose, and it is what the organization does to make its mission a reality.

In the real world, I have found that businesses with a well-defined mission and vision are more successful than those that do not. This is because employees are more engaged and motivated when they know what they are working toward and how their work contributes to the purpose of the organization.

When a business has a clear mission and vision, it is easier to make decisions about how to allocate resources, how to develop products, and how to market services

3. How can a leader empower the people they're leading?

I once asked my father how he learned to do surgeries, and he explained that they had a philosophy of "watch one, do one, teach one."

I suspect a lot has changed in med school since the 60s, but I like the approach - show someone what great looks like, and then give them an opportunity to do the job themselves.

As a leader, it's important to be nearby as a resource they can turn to when they need help, but it's great to let people make their own small mistakes along the way as part of the learning process.

An ex-military colleague of mine describes it as "letting people do things that might cause them to lose a finger, but not a whole arm." And while perhaps I might not want to go to quite that extreme, a great leader knows which mistakes are worth making in order to drive their teams to learn how to thrive in even bigger situations down the line.

4. Who are some of the coaches or mentors in your life who have had a positive influence on your leadership? Can you please tell a meaningful story about one of them?

As a bright-eyed 20-something, I went on a fundraising call to Peter England to ask for his support of a homeless organization I was volunteering with. He was the former CEO of the Elizabeth Arden company and had also been running the Chicago Children’s Museum as an interesting retirement project for a few years. I expected to leave the meeting with a check, and perhaps a business contact I’d call on from time to time.

For some reason, he decided to take me under his wing, and he and his wife Carol became like another set of parents to me.

Over the years, Peter did, of course, have a lot of great advice to offer me as I worked through a series of executive roles. But beyond that, he had a wealth of great advice about how to be a good person, an engaged member of the community, a good husband, and much, much more.

I still don’t know why he decided to invest time and mentorship in me, but his advice not only made me a successful business professional, it made me a successful person in life.

5. Leadership is often more about what you DON'T do. How do you maintain focus in your role?

I once worked for a CEO whose career brought him there through the finance ranks. More than most, he saw every issue as one of dollars and cents, and he taught every leader that they needed to delegate every task to the lowest-cost resource who could successfully do the work.

Doing so would free up the leaders’ time to work on the most complicated, most high-impact tasks that only they could solve, which included training and developing others so that there would be more than one individual in the organization who could do those tasks. It's hard to put into practice because I'm the sort of person who sees a problem I can solve and immediately wants to jump into it and get it done.

With that CEO's lesson in mind, though, I constantly remind myself that "just because you can, doesn't mean you should" - and try to encourage my team members to do the same.

6. If you fail to plan, you plan to fail. Everyone plans differently. How do you plan for the week, month and years ahead in your role?

As a sales leader, I'm used to talking about our annual plan. And a good one isn't just about setting a top-line revenue number; it's about understanding each component that contributes to it - the customer renewals, the price increases, the sales of new products to existing customers, and the completely new logo sales we will do in the year.

In building the plan, I spend a lot of time aligning with my C-team colleagues on the customer retention rates, the marketing leads, the potential product investments, and other items that we believe will be in place to support those goals.

And then, of course, life happens. There's a military saying that "No plan survives first contact with the enemy." We all know that a real sales year won't go perfectly according to the plan laid out on our nice spreadsheet. And that's why I circulate a weekly flash report to all of our stakeholders and keep a close eye on our progress.

7. What advice would you give to a young leader who is struggling to delegate effectively?

My advice to a young sales leader struggling with delegation is this: Remember that 'what got you here won't get you there.'

You were probably promoted because you were a top-performing individual contributor. It's easy to fall into the trap of thinking you need to be a 'super-seller' who does all the work yourself, because that's what got you to where you are. But that's not leadership. At some point, your own efforts will max out, and the tasks will overwhelm you.

Instead, focus on teaching and empowering your team to do what you can do. Think back to that CEO who encourages delegating tasks to the lowest-cost person who is capable of doing the job. Doing so frees up your time to focus on the more complicated tasks that only you can do. It develops your team's skills and confidence. And it creates a culture of shared learning and growth.