The most important strategic action you can take

There is a critical strategic activity that requires attention at this time of year. Do it for your benefit, neglect it at your peril.

That activity is setting up an annual calendar.

It’s a hack. You’ll need to balance team leave and client deliverables and financial year-end and school holidays and a whole lot more.

But if you do it, you provide clarity to your team, you give them certainty.

Being proactive shows your team that you understand. It gives them confidence.

Being transparent shows that you trust them. It shows that you care.

It removes anxiety. It gives them space to breathe, together with a new breath, knowing there is a date and capacity set aside to discuss the direction of the organisation.

The dichotomy is that there’s rarely a time when planning feels right. There is always something more urgent, or another fire to extinguish.

The antidote is intentionality.

Intentionality vs. innovation

Some would argue that innovation, creativity, responsiveness, fluidity and agility are all enviable qualities that fly in the face of intentional planning. Quite the contrary.

The most creative artists set boundaries in place.

The most agile organisations spend time on planning.

“Usually what goes wrong is that you get into the year, people get busy, you get distracted. That’s when you fall into this week-to-week, month-to-month pattern of, ‘Well, what should we do next?’ and being reactive to whatever’s right in front of you.” 

– Stevie Case, CRO, Vanta

The annual plan

To execute on your strategy, you need 4 meetings.

1.The strategy workshop

• This is done once a year (at least). Sometimes every 6 months makes sense, especially if it’s been a very disruptive period and you need to adjust.
• The intention of it is to gather insights (through e.g. SWOT analysis or PESTLE), which you want from a diverse range of stakeholders, specifically your executive management team.
• The format would be presenting insights, brainstorming ideas and then making decisions. You’ll need two things here: firstly, some decision-making framework like an Eisenhower matrix, McKinsey’s three horizons, or a DVF analysis. Secondly, you need to know what success looks like for a strategy output; examples of this would be 5 strategic choices or a strategy cascade.
• Ultimately, you’d want to answer the question “what are the big strategic decisions we’re making to ensure we’re progressing towards our ambitious long term goals?”
• To truly get into strategic discussions and make decisions will take at least two days, and it’s not uncommon to book four days out of the office.

2. OKR / goal setting

• In the vast majority of cases, we’d recommend this be done quarterly. Sometime less frequently is permissible, specifically if you’re a large organisation where things don’t move quickly.
• The intention is to agree on the most important next steps, based on the opinions of the team. You’d need a common language for goals (this is where a framework like OKRs is great), and an understanding of the difference between goals and tasks.
• Because a lot of opinions will be shared, it’s useful to utilise a facilitator for these sessions. This is where commitments are made, and there must be enough clarity to keep people accountable.
• The question to answer is “which areas do we need to show measurable progress on next, and how do we measure success?”
• Set aside at least 4 hours to do this, probably closer to 6. When you first set OKRs, book out 1 to 1.5 days, and combine it with your strategy session.

3. Leadership check-in

• Do it weekly. It should cover not only strategic elements, but also operational problem solving and communication. If a team doesn’t have challenges to solve, it’s questionable whether they really are a team.
• The intention is for the leadership team (not only executive leadership) to ensure accountability and action, and that the team utilise each other’s skills to solve complex problems. In essence, to increase velocity. The agenda consists of three things: a health check on the organisation (for which you need KPIs or a dashboard), alignment on strategic progress (for which you need OKRs), and time for solving challenges and impediments. We usually recommend the formal agenda be preceded by a quick health check on the leadership team to build trust and relationships.
• The question (as it relates to the formal agenda) to answer is “what is required from this team in order to increase velocity?”. Note that the question does not relate to tasks that have been completed, or a report back on activities. At leadership level, these activity report-backs are typically a waste of time.
• A good leadership meeting is 90 minutes – 30 minutes is spent on progress checks, and 60 minutes is spent on solving challenges and impediments.

4. Reflection

• It’s important enough to mention this separately, but it’s usually combined with another meeting like the OKR setting or strategy workshop.
•  The intention is for continuous improvement, setting time aside to intentionally reflect on the way we work, not just the content we work on.
• The format is fluid and simple – but you need some sort of structure. There are various sets of three questions that will enable an agenda, e.g. “what worked well, what didn’t work so well, what can we do better” or “what should we start, what should we stop, what should we keep”.
• The overarching question that needs to be answered is “how can we work together better as a team?”
• The duration is typically around 30 minutes. It’s probably the most impactful as well as most neglected meeting of all four.

Here’s what the mental model looks like:

There are some other important meetings not reflected above. Some of the most pertinent are:

• 1 on 1 meetings, where leaders build relationship and trust with their team members, deliberately avoiding project delivery conversations and rather showing care for the individual’s growth journey.
• Planning meetings, where OKRs are broken down into granular tasks, enabling continuous alignment and crystal clear understanding of the requirements.
• Ideation and prioritisation, where new ideas can be pitched and analysed to ensure we’re continuously evolving and staying ahead of market movements.
• Deep work, where leaders lock themselves away from all distractions to work on specific problems in the business, to think about the future or understand an industry.

The dreaded meeting

If the idea of more meetings gets your anxiety levels up, you’re not alone. But you might also need to admit that it’s not the right response.

“If we hate meetings, can we be making good decisions and successfully leading our organisations? I don’t think so. There is simply no substitute for a good meeting – a dynamic, passionate, and focused engagement – when it comes to extracting the collective wisdom of a team.”

Pat Lencioni

Meetings aren’t evil. Bad meetings are.

It might feel like a lot, but it’s only a lot if you believe that work only gets done outside of meetings. The meeting is the work.

Change the meeting and you’ll change your organisation. Ensure your run them effectively. Get help if you need.

Merry meeting,

Paul