By Stacy Eads
November 7, 2023

6 questions for your annual retreat

Dive into the six questions every leader must ask to pave the path to organizational success.

Recently, I had the pleasure of being invited to Harvard, along with 75 CEOs from around the globe, to attend a co-hosted event between Dr. David Ricketts and acclaimed business author Verne Harnish. It was the pinnacle experience to walk onto the esteemed campus, capping our year-long 20,000 Scaleups initiative.

As an international group of executive coaches, we’re on a mission to impact 20,000 Scaling Up firms throughout the world, and these CEOs have worked for over a year on their strategic plan toward the four decisions every company has to master to scale their company’s valuation: People, Strategy, Execution, and Cash.

The energy in the room was electric. The chalk from some Harvard University professors was literally cracking and breaking in their hands as they flew through the room, running up and down the steps of the classroom – intently listening to each attendee’s unique leadership perspective. Capturing the notes on the chalkboard wall system was ‘oh so reminiscent’ of scenes from Good Will Hunting or A Beautiful Mind. 

The pages and pages of feverishly taken notes abound. iPhones out, taking photos of all the slides, it was an experience, alright! I was honored to walk the grounds of a 386+-year-old institution and grateful to be in the presence of such innovative minds. And yet, I was reminded that it is the foundational basics of excellence that increase a business’ valuation and exit strategy. 

Some industries thrive in today’s economic conditions, while others are floundering in their sales department. So much has changed since 2020, and the last three years of navigating a global pandemic health crisis, along with supply chain uncertainties and inflation, have taken a toll on some leadership teams. If you are burned out, if you are tired of pivoting, if you are unsure of the next right step toward greatness in a world that feels uncertain at times, I offer you these six questions to ask your most trusted leadership team.

It’s Fall, and most of my growing CEOs will gather their leadership teams in October-January for an annual retreat. The once-a-year ability to get away from the office, surround yourself with team-building games, happy hour drinks, and a whole lot of visionary post-its all over the hotel walls. This is where we think greater than the next quarter, larger than the next year, and truly strategize about The Big Picture.

As trained, certified Scaling Up business coaches, these six unique questions are a way we differentiate from other executive coaching services to build solid foundations for our clients’ business valuations. I’d love to see even more CEOs asking their executive leadership teams these thoughtful inquiries. Dive deep this Winter to get crystal clear on your strategy that drives top-line sales by asking these six questions at your annual retreat.

1. What is the job to be done?

Have your executives watch this short, under 5-minute clip of former Harvard professor Clayton Christensen discussing the job of a milkshake at breakfast. Understanding your product or your service’s actual job to be done for the ideal client makes improving that product or service much easier.

Do you truly know, from the consumer’s mind, what the job to be done is? Are you meeting or exceeding their expectations with your products and services based on their perspective of the job to be achieved?

2. Who is the core customer you do that job for?

If you try to be all things to all people all the time – then you will fail to create raving fans because you’ll never truly know your customers well enough to form a deep, impenetrable bond. As a coach, when I hear, “We can do anything for anyone,” that’s quickly translated to “We do nothing for no one in particular.”

By fully and clearly defining the person most likely to buy your services, you will be able to answer the key question: who is the core customer that you do ‘the job of a milkshake for?’  

Who will honestly get the most value from your products? This is your ideal customer. The faster you find them, the faster they can find you.

It’s not enough to only define the basic demographics of advertising – age, sex, education, occupation, etc. You must look deeper at the psychographics to explore how they think, act, and feel. What do they specifically appreciate and value about your product? What motivates them to buy your services? Knowing their needs, their pain points, their wants, and desires is imperative to sincerely create a buyer persona. 

3. Where is the constraint to delivering your ‘job to be done’ to this ‘specific core customer’?

The late Eli Goldratt’s Theory of Constraints, found in his best-selling book, The Goal, suggests that organizations can achieve their goals by identifying and leveraging a system’s constraints. A constraint is something that limits your performance. His theory assumes that there is always at least one constraint, if not more.

For example: Where is the constraint externally among your industry as a whole? Something that you see as a weakness across many of your competitors. It’s assumed as a universal truth that you simply can’t do anything about. But can you???!!

Where is the constraint internally among your team, your products, and your processes? The quick and easy answer is not enough time or not enough people. But don’t let those be the only responses. Dig deeper, unlock new voices, and hear from others on your team. Find the gemstone hidden deep under the surface-level answers.

4. How can you control the constraints in your industry?

If you have not read Verne Harnish’s Scaling Up: How a Few Companies Make It…and Why the Rest Don’t, now is the time. Even if you’ve read the book over the last ten years – I’d highly suggest you purchase a new copy. 2023 was Verne’s 20th anniversary of his first book, The Rockefeller Habits, so he revised BOTH books with new stories and new case studies, and the 2023 Scaling Up revised version even has an entirely new chapter on Exiting your Business.

You’ll see the same purple cover when you go to Amazon or your local bookstore, but within the pages, you’ll unleash the power of thinking outside the box on how to control the constraint within your industry to gain a 10x advantage over the competition.

5. Action: What is the first domino or lever to pull to start controlling that constraint?

If you’ve clearly identified one or more constraints within your company and your industry, now you’re ready to do something about it. Define how you will control each constraint. Then, identify the very first step. Assign a person or a team to that first step, and you’re off to the races, as they say.

If you don’t know, if you struggled to answer number 3 or number 4 questions above, then your next step is to surround yourself with a board of advisors and a business coach. List at least three people who influence your industry or an adjacent industry of the constraint. Start interviewing business coaches to find a good fit. 

Assemble a team of experts. Then, ask them the 6-question exercise to help you uncover what you don’t know. 

6. What is the name of this strategy?

To quote Verne Harnish at Harvard last month, “You don’t have a strategy unless it’s named.” To truly get clear on: What is the job to be done? Who do you do that job for? Where is the constraint in delivering that job to that core customer? How can you control the constraint? And what’s your first action step to controlling it? We recommend Naming the Strategy so you never lose sight of the mission at hand. 

All great military missions have a name. Your strategy should, too.

Naming it will allow your teammates to rally around the strategic mission and rise above the noisy distractions in 2024. Humans can form an emotional, visual, and verbal connection of the senses to feel like they are a part of something bigger than themselves when the entire team has a shared rallying cry.

I hope these six questions to ask in your next annual retreat stir an awakening within your core leadership team. It’s my purpose as a Scaling Up Business Coach to serve executive teams who want to scale their company beyond the status quo. It’s my role to push them, ask the tough questions, and hold them accountable to their own dreams.

It’s not a job; it’s a passion. If you or your team need a facilitator for your annual retreat, or you’re considering the better method of quarterly strategic planning sessions, visit my website for more information on how to get started: Email me directly if you’d like to request a 30-minute personalized coaching session on these six questions:

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About Stacy Eads

Edmond native & UCO Alumna, Stacy Eads, is an award-winning “Most Admired CEO” who scaled her company as a Woman in Tech before becoming an International Scaling Up Business Coach. She now empowers other CEOs from $2M to $200M to embrace their leadership potential through quarterly strategic planning. Her talent is in high demand to CEO Coach, Train Teams, and Speak at Events in both the U.S.A. and Canada.

Stacy Eads’ career affiliations include 50 Women Making a Difference award, Circle of Excellence award, Torch Ethics award, Most Admired CEO award, Edmond Chamber & UCO Mentor, Better Business Bureau of Central Oklahoma Board of Directors, TEDx OKC Speaker Coach, and Ambassador Chairwoman for the Greater OKC Chamber of Commerce.