A CEO's Take: How to Get Your Team Aligned Around a Practical Approach to Strategy

By Mark Goldstein

I don’t have to tell you that the job of a CEO is hard. And aligning your leadership team to work toward an agreed upon and collectively owned strategy is some of the hardest work of all. When I served as the CEO for two very different companies, I learned the best way to bring this alignment about is through offsite strategy workshops. I view a practical approach to developing strategy as a team, which I outline in this article, as essential to the success that we were able to achieve in both companies.

You may have less than positive feelings toward strategic planning events. I know I did. How many have you been involved in? How many of them left a lasting positive impact on your organization? Six months later, were they viewed as time well invested or perhaps a waste of the most precious commodity of any leadership team? Did they lead to greater alignment or less? While these events can certainly be a waste of time and money, if done right, they will lead your team to alignment and growth. Here’s how I saw this to be true…

When I assumed the CEO role for the first time, I was taking over from a very successful founder who was ready to retire. He didn’t want to sell the company before he gave a new CEO the chance to grow it and broaden its value proposition. The company was hugely successful, still owned by its founders, and very profitable. It was not broken!

My focus at this time was to realign the team I inherited, along with some newly hired execs, around a more growth-oriented trajectory. I didn’t want to risk breaking anything fundamental in the process or leave a serious blemish on how my new leadership team viewed me. Using brute force to realign my team was entirely inconsistent with my approach and style, so I decided, despite my past experiences of ineffective strategy workshops, I needed to give the process another shot.

As CEO, I was in a position to clearly articulate what I did not want this process to look like, and with assistance of The Raffoni Group (I was a client at the time), to describe what I did want it to look like. I was crystal clear on my main objective—to end up with a well-articulated strategy that the entire leadership team genuinely helped to create and own. I wanted the strategy to be measurable and accompanied with concrete action plans, and I needed a plan to govern the leadership team around the strategy, without neglecting other operational priorities. And finally, I needed a plan to align the entire company around our new growth-oriented trajectory.

The team and I engaged in the process and experienced great results, so much so that I continued to use it in this company and brought it with me to the next. In my second tenure as a CEO, I found myself leading a company that was the product of multiple acquisitions that left it unintegrated and with several sub-cultures. In this case, we developed a new set of cultural norms, but we kept this distinct and separate from our strategic goal setting.

You may be asking, what about vision, mission and culture? Did you cover these in the process? While these are all important, I view them as a means to an end, and not part of the key deliverables from an offsite meeting focused on developing strategic initiatives.

There is certainly a vision component in this practical approach. The CEO is responsible for setting the vision and should kickoff a strategy workshop presenting his or her view of the next three years. This must include an inspiring reminder of the opportunity that the organization is striving to realize.

The top four key deliverables resulting from a successful strategy development workshop are:

1.    CEO’s vision for the next three years. A rolling three-year time horizon for an ongoing strategic goal-setting process is ideal. The work of the CEO to crystalize this vision should come in advance of the strategy offsite.

2.    Strategic goals with measures of success and one-year targets for each measure. Each goal should have a leader or executive sponsor, a team, and an action plan. The number of strategic goals should be three to no more than five, depending on the capability and maturity of the leadership team.

3.    An internal governance plan that will describe how the leadership team will work with and support each other, thus collectively leading the company in a unified direction. This should include an ongoing commitment to dedicated strategy “check-up” meetings and any other meetings needed.

4.    An organizational alignment plan that will describe how the entire company will be engaged.


While this is a lot to accomplish in what is typically a two-day offsite, it can be done. Include these key ingredients to ensure success:

1.    Participant pre-work – Put this at the top of the list. All participants should be made aware of the deliverables up front and be asked to spend several hours completing participant pre-work that will have a direct tie to these deliverables. This also has the added benefit of avoiding hidden agendas.

2.    CEO presentation – As mentioned above, the CEO kickoff presentation should be prepared ahead of the meeting, and when presented, be clear and crisp. This is the CEO’s opportunity to set a direction that the team can rally around. After this presentation is delivered, the CEO transitions to a participant alongside the rest of the leadership team.

3.    Take it offsite – The strategy workshop should be offsite and away from daily interruptions. No laptops and no phones at the table if possible, if not, then put them on vibrate.

4.    Professional facilitation – Have a skilled facilitator to lead the process from cradle to grave, whether this is someone internally who has been trained in facilitation or hiring a firm, like I did when in the CEO role. This person’s role should include interviewing the CEO and all other participants, assisting with the CEO presentation, compiling the pre-work, facilitating the workshop, and ensuring that the team completes the agreed upon deliverables.

When it came time for me to enter the semi-retirement phase of my career, I quickly concluded that facilitating strategic planning workshops is one of the ways I wanted to spend my time. Given my passion for this approach and my desire to advise and mentor CEOs, it was an obvious choice for me to move into a role of doing both. I’ve come a long way from those early days of not seeing results from these strategy sessions – now I can’t imagine any company finding true success without them.

For more detailed specifics on how to run a high-impact offsite strategy workshop, read Melissa Raffoni’s article 6 Tips for Running Offsites that Aren’t a Waste of Time.