The Future Is Borderless: A Guide to Strategic Coaching

Strategic coaching with a team.

Improve your management skills – and your company’s bottom line – with strategic coaching.

Key Takeaways:

  • Owners need to have confidence in their managers that they can get the job done
  • Understanding culture is essential in managing your team and growing your company
  • Strategic coaching can guide companies through tough periods and into prosperity

Entrepreneurs in the IT world face many challenges – how to grow quickly and smartly, how to maximize profits, and where to turn for advice when you need it. Luckily, there are strategic business coaches who can help.

In this episode of DOXA’s “The Future Is Borderless” podcast series, Founder and CEO David Nilssen hosts Jamison West, co-founder of ConnectStrat, a company that provides strategic coaching, facilitation, and guidance for managed service providers (MSPs) and IT solution providers.

Below, we explore the major takeaways from the episode – how leaders in the tech space can accelerate growth through coaching, Jamison’s background in the IT and MSP worlds, how he grew his company Arterian through acquisitions, and how ConnectStrat differentiates itself from other coaching firms.

The journey of a helpful geek

In addition to being a trained business professional and entrepreneur, Jamison West is also a self-declared geek. He applies his love for all things tech to helping other entrepreneurs get started. Eventually, he decided it was time to build his own company.

In 1995, he started Jamison West Consulting Services (JWCS), an MSP that helped companies in the Seattle area with everything from hardware to email to software to security. In 2011, he rebranded the company as Arterian and found himself hitting a growth ceiling. Over the next 24 months, he acquired four businesses that propelled his company from a staff of 10 to 40, an aggressive plan that brought with it some growing pains.

The challenges of quick growth

A CEO and owner holding on to a rocket and rising fast.

As Jamison quickly discovered, there’s only so much you can learn about a company before you acquire it. You can do all kinds of due diligence to learn about a company’s balance sheet, contracts, legal issues, and the standard measurements of an organization’s health. But it’s much more difficult to perform due diligence on a company’s culture.

In those four acquisitions, the tactical and financial integrations went off without a hitch, but Jamison didn’t know the people that worked in these new companies nor their clients. This became the primary challenge in effectively synthesizing these organizations. 

Once the problem became apparent, Jamison and his team created a culture guide using input gathered from the entire staff. After an epic meeting where all these issues were openly discussed, the overwhelming response was positive (despite a few departures), and the culture improved dramatically.

The emotional journey of selling the company

Saying goodbye to a company you built from the ground up is never easy. But when you’ve invested 21 years of your life in it, selling it can be a real emotional roller coaster. Jamison found himself in this position in 2016 when the time came to move on to his next adventure.

He didn’t widely announce that he wanted to sell, but instead, he let a few professional colleagues know and had four or five suitors show up almost immediately. That was the easy part. The hard part came in watching how it affected the people in the company. It was, in some ways, a brutal process to go through, but it ultimately allowed him to move to the next phase of his entrepreneurial journey.

Writing a book

The experience of selling Arterian was so impactful on Jamison that he felt compelled to write about it. The result, The Emotional Side of Selling a Small Business, is “an entrepreneurial fable” that spins a fictionalized version of his experience, shines a light on the lesser-known emotional impact of selling a company, and aims to help other owners be prepared for that challenge.

The book borrows heavily from Jamison’s own experience and includes case studies from people who’ve been down the same road. His hope for the book was to provide a deep dive into a subject that few other entrepreneurs/authors tackle – the dramatic emotions and surprises that can kill a deal. Other topics in the book include contract structures, valuations, where to find quality buyers, the hidden hazards of succession planning, and what to do after the sale is completed.

A new company

Jamison’s current venture – ConnectStrat – provides strategic business coaching for IT firms. They work exclusively with managed service providers (MSPs), information technology service providers (ITSPs), communication service providers (CSPs), and others in the technology space. Their clients generally range in size from a few million dollars to $20 million in annual revenue.

ConnectStrat’s coaching consists of a simple, four-step process:

  • Vision: Aligning the leadership team on a shared conception of the company so everyone’s rowing in the same direction.
  • Strategy: Now that there’s a shared vision, working with the larger team to focus on how exactly you will accomplish it.
  • Execution: Instilling discipline and accountability in company leadership so they can meet (and eventually exceed) expectations.
  • Impact: Articulating how the owner and leaders are having a positive impact on their own lives and those of the surrounding community.

The company uses an array of tools to successfully implement these four pillars and help businesses grow and prosper. They work closely with owners and those second-in-command to help them understand their company culture.

The biggest mistake business owners make

Through his work as a strategic coach, Jamison has gained some wisdom on how business owners can avoid common mistakes. The biggest of these is an inability to trust your up-and-coming leaders. It’s not always easy to recognize when it’s time to hand off responsibility, but it’s surprisingly easy to micromanage potential new leaders within your company and undermine their ability to grow.

One of the most powerful outcomes of Jamison’s coaching is seeing a company trust its leadership team with “absolute ownership” of its operations. It’s a recipe for success and continued growth, no matter the industry.

Four reasons to consider strategic coaching

As Jamison’s experience demonstrates, strategic coaching can benefit an entire organization, from the veteran CEO down to the rookie executive assistant. Here are some of the major takeaways from his experience and countless others who have reaped the benefits of this kind of mentorship.

  • Enlightened leadership: When you equip owners and CEOs with practices that allow them to listen closely and communicate effectively, you improve their ability to receive constructive feedback, settle disputes, and get buy-in on the ideas that are most important to the company’s success. 
  • Boosted productivity: When leaders and staff feel valued and respected, they relax and do better work. Employees who spend less time stressing about their workplace are then free to focus on what matters most.
  • Positive corporate culture: As Jamison frequently mentions on the podcast, culture is key to understanding and managing employees. Everyone has their own way of working – the trick is to respect everyone’s process while opening the door to new practices that can move everyone in the same direction.
  • Competitive edge: Coaching helps executives introduce new ideas and strategies to take the company to the next level. A well-written strategic plan gives everyone a say in how to move forward and also considers market shifts on the horizon that could signal new and exciting opportunities.

These represent just a handful of the many benefits that strategic coaching can provide to a business, whether it’s a mom-and-pop firm or a multi-million-dollar giant of industry.

Build a better team

Strategic coaches like Jamison West bring decades of experience to their work, building the problem-solvers, innovators, and decision-makers of tomorrow. They motivate leaders and supporting staff alike to create a positive and productive work environment that allows everyone the opportunity to succeed.

Whether you’re motivating your current team to do its best or assembling a new one from across the globe, DOXA and ConnectStrat are there to help.

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