Six-Point Checklist For Your Next Strategic Collaboration

Collaboration appears to be the organizational skillset of the moment. Moving from a “command and control” to “communicate and collaborate” management style has become the de facto leadership mandate of our times.


Even if most of us aren’t particularly good at it, everyone has learned that to not espouse collaboration is to risk getting pigeonholed as old-school. The challenge is that there are two very different collaboration models, one that we’re fast becoming relatively adept at and the other representing new territory that we enter at our own risk–and rarely productively.

The first collaboration model has to do with tactical and executional collaboration, specifically the assembling of subject-matter experts to work together to create something (hopefully) great. The rapid growth of technology-driven innovation has made it nearly impossible for any individual or team to possess all the skills required to create value within one group or organization. And as a result, collaboration among like-minded subject-matter experts is simply how things get done in a world increasingly driven by information and technology. We’re all fast becoming relatively practiced in this form of collaboration, and while some of us are unquestionably better at it than others, we can all trot out a list of best practices we’ve learned and honed over the years to get along, share ideas, and create great things together.

The second collaboration model has to do with collaborating to arrive at an overarching strategy to guide subsequent executionally and tactically focused efforts. Strategic leadership has traditionally been the job of the CEO, the board, and the executive leadership team. The challenge is that as the pace of change accelerates and the complexity of the strategic issues to be solved multiply, the ability of any leadership team to arrive at actionable strategies is increasingly being challenged. Confronted with strategies that are less and less actionable by teams expected to carry them out, more people have been brought into high-level strategic conversations.

The problem is that bringing more people into these conversations without an appropriate collaboration model is simply exacerbating the core issue of ineffectual strategies that we see holding organizations back. When a lot of people are expected to contribute to a high-level strategy, what tends to happen is group think, with the result being poorly focused, all-things-to-all people declarations of strategic intent that end up sorely lacking either “strategy” or “intent.”

Based on experience managing brand strategy work for more than 20 years and helping organizations “get unstuck,” I’ve assembled a list of six keys to effective strategic collaboration. Note, I could have gone to 10, but then I wouldn’t be practicing the art of sacrifice. And keeping it to five would’ve hindered the ability to take action. It’s a simple checklist designed both as a tool for assessing existing practices as a well as a helpful resource for accessing proven tools for getting more out of your next strategic off-site.

1. Assemble the right people in the room: I’ve found a max of four to six cross-functional leaders is the ideal composition. You need the true leaders of their respective disciplines and/or lines of business. There should be at least three different functions represented, as a true strategy by definition touches at least three functions. And once you get more than six people in a room, without an outside facilitator and some serious process, group think takes over with behind-the-scenes conversations being the only way to move the ball forward.

2. Get your hands on some fresh data: Data is required to foster true insight-driven collaboration. The problem is that troves of data that have been lying around for ages tend to come with their owns sets of legacy baggage and are frequently tainted by association with previously ill-fated strategically led initiatives. So the ability of stale data to spark candid strategy conversations is limited. On the other hand, when you have fresh data, it leads to fresh conversations and interpretation as a team. These group conversations concerning previously untrodden ground are what feed true insight-driven collaboration. It’s only through collaboration around insights that true strategic breakthroughs can occur.

3. Prepare options in advance: It’s an artful balance between having done too much prep work and thus having a “dog in the hunt” and not having done any preparation with the result being everyone is driving blind. The trick is to develop out a few potential strategic options worthy of consideration in advance, ideally at least three and no more than five for the group to kick around, modify, prioritize, and ultimately choose one to make their own. When no prep work is done, too much of the heavy thinking onus falls on the group’s time together, and heavy thinking is never best done by committee. At the same time, if the list of options is too short, it ends up turning into a sales pitch by the poor bastards tasked with creating the options for consideration in the first place. And sales pitches are never good things.

4. Latch onto “enabling constraints:” What are those three to five immoveable posts that will force focused conversation, strategic consensus, and action? I’d hazard a bet that not a single effective strategy has been arrived at without a forcing function–be it D-Day, the iPhone, or Facebook not accepting advertising for its first growth phase. Sometimes the enabling constraints are obvious, like four quarters in a row of no growth. Other times they’re less so, such as a growing disconnect between IT investments and product quality, to the point where soon nobody will be buying the product. Usually there is more than one such constraint, and it’s incredibly useful to list them out for the group from the get-go. And then assess where you arrived at against its ability to solve those constraints.

5. Aim to do things differently “next Tuesday:” A successful strategy begs for action. And there’s no time like the present. Odds are that if a carefully honed strategy doesn’t lend itself to doing things differently next Tuesday, then it’s probably not well-honed, nor is it worthy of being called a strategy. Assembling teams of people for further conversations is not a strategy. Nor is hiring a consulting firm to provide a second opinion.

6. Practice the art of sacrifice: Focus, focus, and more focus is the key to any effective strategy. As well as a critical enabling constraint to turning group thinking into single-minded, actionable outcomes. What is that one singular idea underlying the strategy intent? Write “the art of sacrifice” up on the wall at the beginning of any strategic collaboration session. Discuss what it means. Commit yourselves to arriving at some place singular together. Executional collaboration is all about multiple goals, objectives, and activities. On the polar opposite of the spectrum is strategic collaboration, where a successful outcome absolutely must be singular in intent. If there were ever a place for simplifying, this is it.

Odds are that you’ll be well-served if you manage to employ at least three to four of these guidelines for strategic collaboration in your next strategic off-site. Even if you’re a seasoned strategic collaborator or facilitator, just reviewing this list in advance and sharing it with the collaboration team can create a level of group self-awareness that will result in getting you to a sharper strategy faster. Finally, it’s worth reminding ourselves of the critical differences between executional and strategic collaboration. The latter is absolutely critical to achieving the former. But the models and mindsets required to achieve each of those stages for creating actionable value couldn’t be more different.

Ted Nelson