Aligning leadership and strategy in a growing startup

Context snapshot

Organisation: Strategy software startup

Domain: Strategy tooling, decision support, and professional services

Environment: Competitive, SaaS, capital- and resource-constrained

Growth challenge: Evolve a core enterprise product while exploring new markets and offerings

Leadership need: Align priorities and investment choices as a leadership team

Executive tension

This startup develops software that helps organisations capture and organise their strategy.

As the business matured, the leadership team faced a familiar but difficult tension.

They needed to align on how to:

• Progress and modernise the existing core software proposition

• Renew the architecture using modern engineering practices

• Improve user experience while adding new features

• Retain an enterprise client base while expanding to new customers

• Decide whether and how to support clients with professional services

• Explore a new offering focused on strategy creation

• Attract new customers, smaller size, more volume

The need to address the existing client base by doubling down on the enterprise product was logically emerging. But others saw an opportunity to launch new offerings aimed at broader, higher-volume audiences — potentially competing in spaces dominated by platforms such as online project management tools.

At the same time, there was pressure to generate revenue in the short term while investing in a much-needed user interface refresh and longer-term growth options.

Funds, time, and people were limited.

What mattered most was not finding the right answer, but getting the leadership team genuinely aligned on priorities, trade-offs, and next moves.

Reframing the problem

This was not an unusual startup problem.

It was a flow and focus challenge at the leadership level.

At this scale, strategy cannot be about doing more. It must be about:

• Prioritising ruthlessly

• Sequencing investment

• Creating space for experimentation

• Making cautious commitments only once learning has occurred

The traditional linear view of strategy — problem → solution → plan — was insufficient.

What the team needed was a way to:

• Explore multiple options without fragmenting

• Ground ambition in real constraints

• Generatively think of new ideas and new pathways

• Make trade-offs explicit

• Leave the offsite with a shared baseline and clear direction

Above all, they needed to get on the same page as a leadership team.

How we worked

1. Prepare the ground before the offsite

To make best use of two full days with the senior leadership team, preparation started well in advance.

We:

• Interviewed key leaders individually

• Asked sub-teams to prepare short briefings on persistent problems that were not getting solved

• Invited others to surface opportunities they sensed but had no capacity to explore

This ensured the offsite started from reality, not slides.

2. Use a non-linear strategy exploration pattern

The offsite was designed as a facilitated strategy workshop inspired by Mike Burrows’ Agendashift™ and the IdOO pattern (Ideals, Obstacles, Outcomes).

This pattern creates generative, collaborative exploration rather than forcing premature convergence:

• Ideals set strategic direction and boundaries for focus

• Obstacles grounded the conversation in real constraints — organisational, technical, commercial

• Outcomes centred the discussion on business benefits, not just activity

This helped surface what truly mattered, while encouraging creativity and shared ownership.

3. Make the strategy explicit and coherent

As clarity emerged, the baseline strategy was captured in an X-Matrix, connecting:

• True North

• Strategic aspirations

• Key strategies

• Measures

• Execution priorities

• Required collaboration across the organisation

This made alignment visible and created a concrete reference point for action.

4. Clarify the strategic landscape

During the offsite, we also produced Wardley Maps of the business landscape.

This helped the team:

• See their current position more clearly

• Understand dependencies and constraints

• Explore potential pathways without committing prematurely

Mapping complemented the strategy work by anchoring discussion in context, not opinion.

Evidence of movement

The offsite created immediate and tangible outcomes.

The leadership team developed a clear, prioritised strategy tailored to the realities of the business. Trade-offs were made explicitly rather than deferred. Assumptions were challenged, and obstacles addressed rather than worked around.

Equally important, the dynamic of the leadership team shifted. The facilitation created space for all voices to be heard, strengthening trust and collaboration. The CEO was able to fully participate in the strategy discussion rather than managing the process, increasing the quality of contribution and decision-making.

The result was not just a strategy artefact, but a shared understanding and commitment — a baseline the team could now execute against with confidence.

Inviting your reflection

Many organisations still approach strategy as a linear exercise:

define the problem, choose a solution, produce a plan.

That is not strategy.

It leaves little room for challenge, reality, or imagination — and struggles to cope with uncertainty, constraint, and change.

What might shift if strategy were treated as a collaborative exploration rather than a planning exercise?

And when will organisations reconsider how they do strategy, not just what strategy they choose, in order to achieve better outcomes?

Testimonial

" I was fortunate to ask Philippe to run a two-day off-site strategy session for our senior leadership team at i-nexus. As a CEO, bringing in an external facilitator can sometimes feel like a gamble, but it paid off tremendously with Philippe. We had two lively days; Philippe helped us set some context for our current position and future aspirations, using many different tools, one of which was Wardley Maps, which brought depth to our strategic vision and planning. 

What stood out most was Philippe's facilitation style—calm, reassuring, and thoroughly engaging. He encouraged participation, meaning all voices were heard (and valued), which I believe brought our team closer and meant the strategy was more robust. Philippe would challenge our assumptions and push to address obstacles, which resulted in a sound strategic planning experience.

We developed a clear, well-prioritised strategy tailored to our needs. A personal benefit of having Philippe lead the session was that it allowed me to participate fully and contribute without needing to guide the proceedings; I found this a refreshing change and added significant value to the discussions.

Philippe's professional yet approachable demeanour, coupled with his deep understanding of digital business transformation, makes him an obvious choice as a facilitator. I highly recommend Philippe to any organisation that is aiming to develop its strategic plan (new or an iteration) and begin the challenge of execution. "

Simon Crowther - CEO