Opinion- 7 Reasons Your Strategy Days Aren't Working.


Hello and thank you for reading this.

Today I’m gonna write another of what I’m calling my opinion posts. I haven’t badged it like that before; but I’m taking a risk. Why? because that's what life is about.

The role of a coach is to disturb and provoke thought. You will regret the things you didn't do, more than you will the things you did.

So this post and any other I write under the badge of OPINION opinion with the aim of doing exactly that.

Annoyed by it - lean in. Change my perception. Support my view? Let me know. And, if there is some element of truth in it for you - think about what that means. If you have the influence to do something about it, use it

If you want to change it. Let’s work together, to make it so.

Stefan

7 Reasons Your Strategy Days Aren't Working.

Strategy days are intended to be impactful opportunities for teams to come together, develop actionable plans, and align on their goals for the future. However, if you’ve recently found that your strategy sessions aren’t yielding the desired outcomes, you're not alone.

Drawing from my experiences both in facilitating these sessions and my own leadership journey, including my narrow loss on a recent strategy bid, I’ve identified seven key reasons why strategy days often fall flat.

In this blog, we’ll explore not only the reasons behind ineffective strategy days but also how insights from leadership thought leaders—Simon Sinek, Alain de Botton, Brené Brown, and Jacinda Ardern—can inform a better approach.

Reason 1: Your Team Aren't Really a Team

One of the primary reasons strategy days fail is that team cohesion is lacking. As Simon Sinek emphasises, understanding your “why” plays a pivotal role in uniting a group. If team members view themselves as individuals working toward separate goals rather than a cohesive unit, collaboration will suffer. A successful strategy day should foster a sense of belonging and shared purpose.

Reflect on Sinek's advice: ask your team why they are together and what common goals they hope to achieve. Creating a safe environment where individuals feel valued and connected is crucial.

Reason 2: Your Team Hasn’t Really Committed to the Goal

Even when a team is assembled, a lack of commitment to shared objectives can doom strategy days to failure. Alain de Botton reminds us that meaningful relationships require mutual investment.

Leaders must create a culture that emphasises accountability and shared ownership of goals.

During strategy sessions, engage your team by allowing them to articulate their commitment. Ownership is cultivated when people feel they have a voice in setting directions, thereby deepening their investment in outcomes.

Reason 3: You Don’t Really Have a Strategy; You Have a Set of Outcomes

A common pitfall is confusing a strategy with a list of desired outcomes. True strategy involves a clear understanding of how to reach those outcomes. Brené Brown states, “Vulnerability is the birthplace of innovation, creativity, and change.” Embracing vulnerability as a leader can open avenues for deeper discussions about the shortcomings of existing strategies.

During strategy days, encourage openness to critique the current trajectory. If your objectives lack clarity or the steps to achieve them are nebulous, the session is likely to lead to frustration rather than success.

Reason 4: You Haven’t Really Discussed What Needs to Change in and Across The Business.

Ignorance of necessary changes can inhibit progress. Effective leadership requires honest feedback and a willingness to confront uncomfortable truths. Jacinda Ardern exemplifies compassionate leadership that thrives on open dialogue and candid discussions about challenges.

Strategy days are a prime setting for honest conversations about what isn't working. Establishing trust among participants allows for these discussions, and a skilled facilitator can help guide this process to ensure all voices are heard.

In addition, a successful strategy intervention will hinge on how well it applies across and with the whole business. One part of an organisation working out of sync, cadence or direction with an another means your ‘sails’ aren’t harnessing the prevailing winds. Define interdepartmental change too.

Reason 5: You Have Chosen A ‘Safe’ Facilitator

Utilising a familiar and safe facilitator each time can lead to stagnation. While familiarity breeds comfort, it doesn’t always foster innovation.

Sinek’s emphasis on new perspectives is particularly relevant here; a facilitator who understands the dynamics of change is essential.

A facilitator should possess not only the knowledge of strategic frameworks but also the ability to engage teams in transformative processes without relying solely on positional power. Choose someone who challenges your norms and inspires fresh thinking.

Reason 6: You Held a Strategy Day Rather than a Set of Strategic Interventions

Many leaders conflate a single strategy day with a continuous process of improvement. Strategy doesn’t emerge overnight; it evolves through iterative interventions. Implementing Sinek’s Golden Circle can help ensure that your strategic approaches are aligned consistently with your organisation’s “why.”

Employing a framework like Goals, Reality, Options, Way Forward, Testing and Help (GROWTH) and/or SWOT, PESTLE and KRASH, can structure your interventions effectively, giving participants clear steps to engage with and revise the strategy.

Reason 7: You Let Someone Talk You Out of Running the Strategy Day You Wanted

The final and arguably the most critical reason strategy days may underperform stems from external pressures to maintain the status quo. Listening to others’ reservations can deter the very innovation you’re seeking to achieve. Ardern’s leadership illustrated the importance of challenging complacency in favour of progress.

When crafting your strategy, trust your instincts. A strategy day which aligns with your vision and one which can disrupt existing paradigms is vital. Remember, breakthroughs occur when you resist the urge to conform to the prevailing conditions and the wishes of a stakeholder who is set on maintaining the existing norms.

Conclusion

Reflecting on your previous strategy days reveals patterns that can inform future interventions. The principles shared by thought leaders and my personal experiences highlight the importance of embracing vulnerability, fostering connection, and articulating a clear purpose.

The effectiveness of strategy days hinges on our ability to not only recognise the common pitfalls but to actively engage in the transformative leadership practices that address them. As leaders, we have a unique opportunity to be facilitators of positive disruption. By fostering a genuine sense of teamwork and shared purpose, as Simon Sinek advocates, we create an environment where collaboration thrives.

We must instil a culture of commitment and accountability, taking cues from Alain de Botton, so that every team member feels invested in not just the outcomes, but the journey toward achieving them. Embracing vulnerability and open dialogue, inspired by Brené Brown and Jacinda Ardern, will enable us to confront uncomfortable truths and ignite innovative thinking.

Crucially, let us not shy away from challenging the status quo. Effective strategy days are not one-off events but evolving processes that require fresh perspectives and continuous reflection. By choosing the right facilitators and structuring our approach around our core “why,” we can ensure that each strategy day becomes a powerful catalyst for change rather than a perfunctory meeting.

Some questions to reflect on

These questions can help catalyse thoughtful planning and ensure that your strategy day or intervention is impactful and aligned with your organisational goals.

  1. What are the primary objectives of this strategy day?
    Identify the specific outcomes you want to achieve to ensure that the focus remains clear and actionable throughout the session.

  2. How well do the participants understand their roles and the importance of collaboration?
    Assess the level of team cohesion and ensure that all participants are aligned on the shared goals and the significance of working together.

  3. Have we established a culture of trust that encourages open dialogue?
    Consider the current environment of your team; do participants feel safe to express their thoughts and provide honest feedback during discussions?

  4. What current challenges and opportunities should we address during the session?
    Encourage participants to identify key issues or areas for improvement that can spark meaningful conversations and strategies.

  5. Who will facilitate the session, and what qualifications or perspectives should they bring?
    Determine the best-fit facilitator who can challenge the status quo and inspire innovative thinking in a way that resonates with your team dynamics.

  6. How will we ensure ongoing engagement and follow-up after the strategy day?
    Plan for mechanisms that support accountability and continuous improvement, rather than viewing the strategy day as an isolated event.

  7. What frameworks or methodologies will guide our discussions and decision-making processes?
    Select a structured approach, such as GROWTH, Sinek’s Golden Circle, SWOT, PESTLE and KRASH that aligns with your team’s objectives and encourages a clear, cohesive path toward action.

As leaders dedicated to positive disruption, we must remain resolute in our commitment to creating spaces that encourage honest, open dialogue and foster an ethos of creativity and growth. Let us step forward with courage, challenge complacency, and drive the change we wish to see, paving the way for a future that is not only strategically sound but also profoundly impactful. Together, we can transform strategy days from mere meetings into dynamic collaborative ventures that propel our teams and organisations toward their true potential.

I hope you’ve found this useful and if you’d like to chat through these questions or your strategy day itself get in touch at stefan@stefanpowell.co.uk

I’d love to help you get the most from the time you have.

Stefan :-)

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I look forward to sharing my next OPINION blog soon.

For now; thank you

I am…

An executive coach who specialises in helping good people lead great things.

Good people care about others, our planet and beauty. Great things are changes for the betterment of society and all that lives within an around it.
It sounds big and fun - it is.

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