One of the most astounding figures to come out of AchieveIt’s 2025 annual benchmark report is that 78% of failed strategic initiatives can be attributed to a lack of collaboration. Collaboration may seem so easy to solve – it’s just encouraging people to work together, right? Do 7.8 out of 10 organizations have employees who simply don’t talk to each other? 

It goes beyond “teamwork makes the dream work.” Strategy execution issues stemming from lack of collaboration start at the root – during strategy creation. Yes, there are adjustments organizations can make mid-planning cycle to improve symptoms, but the seeds of healthy collaboration are most effective when sown during the strategic plan creation process. 

Breaking Down Silos

Contrary to what one might think, most of the time, silos aren’t created out of spite, or even intentionally. Segmentation of work is natural. Silos are often accidentally created when people forego the gathering of many minds for additional input and perspective because it’s too challenging to find time that works for everyone. And what an expensive meeting that becomes!

It’s like the old adage haunts, “If you want to go fast, go alone; if you want to go far, go together.” Lack of patience and commitment is the greatest harbinger of falling victim to the 78%. 

Improving Collaboration During the Planning Process

One of the biggest mistakes the C-Suite makes during strategic planning is choosing initiatives in a silo. Without a doubt, the most successful plan building method is to build from the top-down, and then bottom-up. Every level of an organization has a crucial role to play in the building of a strategy. If any one of those groups is not included at all, or otherwise proceeding with the wrong expectations, the lack of necessary collaboration will result in a malformed plan. 

Collaborative Plan Building Roles

Leadership

Leadership’s job is to set a clear direction.

Executives should do plenty of research before the first planning session – reading studies from without and outside of their industry, interviewing customers, polling the larger market – to enter into the conversation with a clear concept of short term goals that can help reach the organization’s overall Vision. 

This usually means 50 initiatives enter the board room, and 10 walk out. 

The organization’s leader needs to be clear about several things, including but not limited to: 

• How strategic initiatives will be chosen: They should be judged on how effectively they’re expected to help achieve the Vision. 
• How many initiatives will make it to the next round: Don’t shy away from putting a number on it. By stating the cut off upfront and concretely, everyone knows exactly what to expect. 
• What comes next: The steps in the plan building process should be thoroughly explained to this group, to help message expectations to their groups. 

Director-Level or Middle Management

After leadership narrows the focused list of possible strategies, the next level of management should be looped in to give perspective and feedback from closer to the front lines. Middle Management’s role is that of a Democratic Republic – they are representatives of their direct reports and their perspective on the work to be done. 

Each Director should enter into the conversation armed with knowledge from their employees: what is the resource cost for certain tactics, how long do certain projects take, what sort of staffing or reorganization will be needed to support new goals? During this stage, the semifinal list of 3-4 strategic focuses for the plan should emerge for Leadership to finalize. 

The Rules of Engagement that should be set by Leadership at this level include: 

• Not every initiative will be chosen: Executives should communicate well in advance to Middle Management to come prepared to defend initiatives they expect to be the most impactful. 
• Everyone leaves the room aligned: Leadership needs to make clear that the chosen initiatives are in the interest of the organization and there should be no hard feelings due to perceived wins and losses (ownership).  

Pro Tip: Use Expectation Setting Phrases

Couch things that might receive pushback with a starting phrase that acknowledges the expected reaction. 

“This might sound harsh, but we can’t leave this room until we’re all aligned in order to achieve success.” 

“This might make me sound like a jerk, but if your initiative isn’t chosen, don’t take it personally; we’re making tough decisions today.” 

By stating concerns before you hear them, this can help relax the room and get people on the same page before beginning. 

Check out what Chris Voss has to say about negotiation in his Masterclass on Tactical Empathy: 

“The stereotype is that I win means you got to lose, and I beat you. That is not the case. Great negotiation is about collaboration. It’s about several people faced with different aspects of the same problem. The adversary is not the person across the table. The adversary is the situation. The person across the table is a counterpart that’s struggling with some aspect of the same problem that you are. You work with them and solve that problem together, and you’re both better off.”

Collaboration During the Execution Stage

If an organization did not build their plan from the top-down and bottom-up however, execution is not lost! There are still collaborative habits to build now, mid-plan, that can raise the floor of success. Collaboration during the plan execution stage is not gathering all employees in a room and not letting them out until each initiative has two names on the owner line. The goal is to allow professionals to operate at their highest ability, but increase communication between those experts to share insights and resources. 

The Fine Line Between Collaboration and Too Many Cooks in the Kitchen

Many hands can make light work, but in the case of strategic execution, they can also spread focus too thin, “like butter scraped over too much bread” (J.R.R. Tolkein). Organizational leaders are hired for their specific skills and expertise, so those professionals should be all in on their initiatives – but that doesn’t mean they need to be heads down. It’s a delicate balance to be able to include enough perspectives and feedback without losing time. 

Collaboration Isn’t About Sharing the Work, But Sharing Insights and Perspective

Working together doesn’t always mean sharing action items, but rather working in tandem in alignment. Communication is key. During monthly strategic plan status update meetings, it’s important to share findings and resources to ensure teams are working most efficiently and not doubling efforts. Time together should be spent focusing on barrier removal, information sharing, and resource consolidation.  

Leadership should create the desired atmosphere by diving into the key findings and asking directors to speak up about specific highs and lows. This will instigate an engaging cross-table discussion where people will feel they have more to share. It changes valuable time together into time that couldn’t be replicated by reading a document.  

Strategy Execution Software is Helping Organizations with Collaboration

The good news is that, like most of the key takeaways from the 2025 State of Strategy Execution Report, the reason strategies fail isn’t due to the wrong or missing ideas. 

The top reasons strategic plans don’t succeed are due to the efficacy of the rules of engagement and governance around your plan – which is something that can be achieved with the right guidance.  

Reach out to one of our Execution Experts for a customized understanding of how AchieveIt can partner with your team to help set expectations for collaboration on building and executing a strategy.