STELLAFAI EXPERT SERIES

Top 3 strategy execution challenges for organisations

Stellafai
Stellafai
Published in
6 min readJul 21, 2023

--

Welcome to our Expert Series, where we make expert knowledge accessible to all, empowering you to achieve greater success. Twelve bright and brilliant minds have generously shared their wisdom so we could package up for you. In this instalment of our Expert Series, we are uncovering the greatest challenges organisation and their leaders face when executing their strategies. Forewarned is forearmed 💪 so you can these treacherous pitfalls and dodge those strategy execution sinkholes! 🕳️

🤫 Psst — If you’re in a rush and want a speedy summary of our expert’s wisdom, skip to the end to hear what Stellafai’s AI-powered Digital Assistant key takeaways were!

Gerri Vereen, OKR Coach & Thought Leader

1. Missing connection to Mission and Vision.

2. Weak management support.

3. Failing to engage employees.

Scott Ambler, Co-developed Disciplined Agile Delivery & Author

1. Getting everyone aligned.

2. Understanding what the market needs, and when it needs it.

3. Guiding the organization through the multitude of AI-related changes this decade.

Claire Donald, VP of Technology & Product at Moo

1. Wider organisation not being clear on what the strategy actually is.

2. Team not understanding how their work contributes to that, leading to misalignment.

3. Trying to do too much at the same time.

Alexis Monville, Agility & Leadership Coach & Thought Leader

1. Alignment Behind a Concrete Vision: Many organizations struggle to define and communicate a clear and concrete vision. This isn’t just about having a grand idea; it’s about articulating what the organization is trying to change, and for whom. It involves defining a purposeful direction for the product or service that all team members can understand and rally behind. A well-articulated vision not only guides strategic decisions but also motivates teams by giving them a clear sense of purpose.

2. Connecting the Dots: Translating the concrete vision into actionable steps is another significant challenge. This involves mapping out the path from the present state to the envisioned future, breaking down the journey into manageable objectives, strategies, and tasks. It’s about ensuring that every team member understands their role in this journey, fostering cross-functional collaboration, and breaking down silos.

3. Measuring What Matters: Choosing the right metrics to monitor progress towards strategic goals is crucial. However, it’s often a challenge to identify the metrics that accurately reflect the progress being made. This becomes even more complex considering that different stages in the life of a product or service may require different measures. Therefore, it’s critical to focus on metrics that directly indicate whether the organization is moving towards its vision.

Carsten Ley, Founder of OKR Asia / OKR Expert

1. Strategy is not shared or clear to everybody.

2. Short term actions and projects are not linked to Strategy.

3. The Strategy is not up to date.

Sue Lueder, Agile Thought Leader & OKR Evangelist

1. Being ambitious enough but also knowing when to pivot and redirect resources.

2. Large, heavy-weight annual planning exercises that drain resources during Q3 which should normally be the most productive quarter executing on the year prior strategy. (i.e. no continuous planning muscles)

3. Transparency into many diverse programs and seeing the forest through the trees.

Hannes Albrecht, Founder at how-to-okr.com / OKR Expert

1. Lack of focus, when companies try to tackle everything at the same time.

2. Weak or non-existing cross-functional alignment.

3. Companies don’t use or stick to a short planning/ execution cadence. Cadence is everything.

Bart Den Haak, Author of Moving the Needle with Lean OKRs

1. No strategy defined.

2. Dysfunctional leadership.

3. Siloed goal settings.

Max Bicknell, Agile Coach & OKR Evangelist

1. The biggest killer in my experience is the age old problem of too much WIP. There’s a tendency to go after all the goals as soon as strategies are created and this leads to all the progress moving at too slow a pace. This often, decreases trust, which leads to more course correction from leaders & less autonomy for teams, creating a vicious cycle that slows things down even further.

2/3. The next 2 for me are really closely tied together, and they are having either no objective way to measure progress towards your goals (e.g. lots of outcomes that start with words like deliver or execute), or choosing metrics that are more lagging indicators of success. The impact of both of these challenges, is that you end up in a cycle of charging towards the end of your review cadence to try to call the thing done without knowing if it’s going to have the impact you want. They both feel more output focussed for teams, and ultimately mean that the organisation is making much bigger bets in investing time and effort in these types of areas.

Evan Leybourn, Founders of Business Agility Institute / Agile Expert & Author

1. Letting go of strategy when new opportunities or learnings emerge. (sunk-cost fallacy)

2. Strategic prioritisation — saying no to things.

Richard Russell, OKR & Leadership coach

1. Clarity about what the strategy is across a growing team, especially as strategy evolves.

2. Translating strategy into actions and decisions — and particularly knowing who should make those decisions and how.

3. Tracking progress in a meaningful and useful way — and relatedly, handling performance management in a context of uncertainty and change.

Brad Dunn, Product Management Leader & Coach

1. Misalignment caused by poorly constructive incentives.

2. Unclear visibility into the barriers stopping people reaching their goals.

3. Not working on cognitive and political barriers towards strategy execution (see blue ocean strategy)

Armstrong here, your trusted co-pilot in Stellafai. I’ve read and digested all these incredible insights from our stellar panel of experts orbiting the business strategy universe. So, to help you navigate the complex cosmos together, I’ve decoded these insights into my top 5 takeaways:

  • Aligning behind a collective vision: A vision isn’t just a statement — it’s a shared journey that the entire organisation should embark on together. It’s critical that every team member understand their role in and contribution to fulfilling this larger mission. When an organisation aligns behind a clear, compelling vision, it engages, motivates and inspires every person to make that vision a reality.
  • Connect & Communicate: Executing your strategy is like building a network of bridges, linking everyday tasks to long-term goals. Without clear and robust communication of these bridges, progress may slow or be in the wrong direction. Effective communication is critical to build those sturdy bridges and help keep us on track.
  • Prioritise: If we overload ourselves by pursuing all goals at once, progress will be slow, and there’s a high risk of burnout. Focusing our efforts on the most impactful objectives and learning to say no is crucial. Only then can you ensure our efforts drive meaningful progress
  • Strong Leadership: Leadership isn’t just about taking charge — it’s about guiding the team through the twists and turns of our journey. We count on our leaders to chart the course, keep us moving in the right direction and support us when we need it. Without strong, supportive leadership, the journey towards achieving goals and change will be hampered by the gravitational pull of the as-is.
  • Overcoming Obstacles: Cognitive and political challenges are almost guaranteed to arise on the path to strategic execution. Embracing, learning from, and adapting to these challenges can make us more resilient and adaptable, ready to tackle any hurdles we encounter.

www.stellafai.com

--

--