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How to...Prepare for a Strategy planning session - Free assessment

Updated: Jul 5, 2023

It's time again to review you strategy. A day or two away from the business to work on the business. It can be highly productive, or it can be a big talkfest without clear or good decisions and commitment to action!

To avoid this, I recommend everyone is well prepared ahead to get the best possible thinking, engagement and decisions on the day.

Although it is hard to step away from the operations, the real villain is the absence of a strategy planning routine and effort in good preparation.

A quarterly discipline is vital during the scaling process. If done well, together the team will make strategic decisions, set goals, align everyone on priorities and commit to action for the next quarter.

Here is a checklist of how you can prepare well, to avoid wasting time on the day or worse walk away with a lack of high quality decisions and commitment that actually move you closer to your purpose and long term goals.

Be Prepared

In the words of Scar's Jeremy Irons in Disney's Lion King - Be Prepared.

Schedule your strategy session a few weeks in the future to make sure you and your team have time to prepare (in between everything else on your plates!)

A lack of preparation may result in many folks coming to the session with their mind still on executional or operational tasks. Meaning it takes longer on the day itself to get everyone's head in the game and thinking about more strategic questions and shifts facing the business.

It also means people have more time to think and plan ahead and bring more fact-based information to the session, versus operating on hunches and perception.

Finally it highlights who on the team has energy for strategy - not everyone likes it. Among your team try to identify those with strategic thinking capabilities, and may be potential additions to more frequent strategy discussions such as held by a strategy council.

You don't necessarily need a detailed Agenda when you send out the date, but it's a good idea to have some key questions or areas you want to address in mind.

Perhaps these are related to changing customer sentiment, or tensions between structure and culture, or how to streamline processes and increase automation. Or maybe it's unknowns around funding and working capital for growth.

Get input ahead of time on these questions by using the strategies below. This gives you time to gather data and input and finalise an agenda ahead of the session date.

Gather customer data

Data can be quantitative (eg net promoter scores, usage data, customer value measures, financial data, employee surveys), or qualitative. I am a big fan of gathering qualitative data, such as having semi-structured calls or conversations with you customers regularly.

While quantitative data answers 'how much', qualitative data is more suitable for answering "how".

It can provide deeper insights particularly when we don't know exactly what we are looking for.

For example;

  • How are customers handling emerging pressures or challenges facing their industry?

  • How is your firm positioned in your customer's mind versus your competition and expectations?

  • How else can your organisation deliver on its brand promise and outperform versus competition? i.e. how can your organization perform the top one or 2 jobs they need you to do for them >100% and better than anyone else?

How many conversations should you have?

We don't want to overwhelm ourselves with semi-structured data at the same time, we want a good sample of a particular type of customer to see a theme. If your business is relatively simple and you have 1-2 types of best customers cohorts you won't need many customer conversations to reach "saturation" on key themes.

Such conversations can be done efficiently by phone or online and even recorded with your customer's permission, so you can go back through the conversation later and extract key themes and quotes to share with your organisation.

Having discussions with your team around what customers are telling us right now, is a fantastic springboard for brainstorming and get's everyone bonded and focussed on delivering for customers first.

Once you have a good process in place, think about how you can hard-wire such a qualitative feedback gathering and analysing routines into your organization on a more regular basis, to drive "always on" learning and innovation.

Gather internal feedback

Many firms gather internal and employee feedback on a regular basis through engagement platforms or pulse surveys such as CultureAmp, Officevibe or even via basic survey tools like Typeform, SurveyMonkey and Google forms.

Ahead of strategy sessions, prepare by sending out a short survey to get input on strategy and priorities. I recommend this be done among those attending but you may also considering sending the same survey to other people in your organization or on your board who may not be attending. Some firms also send surveys to suppliers and channel partners.

It is particularly important to gather input and knowledge from front-liners and operational people who are close to customers, developing products, or innovating new processes and technology as well as those who are in leadership roles or managing cross-functional project teams.

Examples of survey questions you may want to have knowledge of ahead of a strategic planning session are;

  • Strengths and weaknesses in the company today (that are unlikely to change in the short term).

  • Trends they think are affecting your industry, customers, channels, geography, resources or technologies that are used extensively in your business.

  • One thing your company can do differently to accelerate towards your longer term goal/purpose.

  • One thing your company should prioritise in the coming quarter.

It's often surprising how different everyone's response is and reinforces how important a good strategy planning routine is for team alignment.

Here is an example of a preparation survey to send out to your team that gathers input on Brand promises, SWT and Priorities. Feel free to test it out yourself.

Review Strategy

It's also a very good time to understand how well your employees and other internal stakeholders perceive the firm is doing with regards to fulfilling its purpose and core values.

Take some time to review your current Strategy. Often we have a 'set and forget' mentality about longer-term strategic elements such as Purpose, Core Values. Take some time to gather feedback from staff, board and leadership on these, for example by asking;

  • On a scale of 1 to 10, how well they think your organization is doing at living up to its core values and it's purpose/vision.

  • If less than 10 - what your company can be doing to better live up to its core values / purpose.

You can bring the responses into the first part of your strategy planning day to keep the leadership team strategically focussed, not just executional or operational.

Structured Assessment

One way to plan your strategy session is to assess your organisation's biggest growth opportunities. The Scaling Up assessment is a good way to do this if you are a small to mid sized business or scale-up.

The Scaling up assessment is specific to your organization and designed to identify your biggest scaling up opportunities. Scaling up offers the assessment free to organizations serious about scaling.

The assessment involves 32 questions covering all areas of the business including people, strategy, culture, operations, processes, technology, data, organizational routines and leadership. It can be sent to anyone, but recommended for the CEO and leadership team as a start.

Results are provided benchmarked versus other firms at same industry, size and scale. As well as the CEO results vs. team average. Which helps understand team alignment on the current situation and performance opportunities.

We usually recommend every CEO and leadership team perform a Scaling up assessment at the start of any Scaling up coaching engagement. This helps to prioritise a coaching engagement plan, including strategy and planning facilitation, first on the biggest scaling up opportunities within your organization. You can try it out for free - just click the link below.

Get external impulses

We want to create the best environment for diverse and strategic thinking we can. One way to do this is to gather external impulses from people outside the firm.

Scale up founders often find it useful to speak regularly with other CEOs and leaders within ther broader industry. Or leaders / operators of organizations with similar business models and a few stages ahead of them.

Another way to provide external impulses and inspire strategic thinking in your team is through compiling some pre-reading or resources and circulating these ahead of the meeting.

Articles or videos on a trending topic you would like to emphasise or challenge facing your industry or organisation. For example this article by Clayton Christensen on Jobs to be Done Theory a valuable pre-read ahead of discussing customer strategy and differentiation.

Bring in an external facilitator

An external facilitator such as a strategy planning facilitator or scaling up coach can help by providing new methods and tools to formulate strategy or solve problems.

They can also do more of the heavy lifting to get the most out of a strategic planning workshop, allowing the entire team including the CEO to fully focus and lean into the discussion, contributing in equal measure.

A scaling up coach will also provide guidance on preparation ahead of the day and meaningful feedback and guidance during the session to sharpen your strategy, plans and decisions.

In summary...

Whether your next strategy or planning session is for 4 or 40 people, proper preparation will help ensure everyone is contributing strategic thinking and making better decisions during the session. A coach will help you to plan, such as deciding who should be invited, what to prepare, and how to craft an agenda that gets to the outcomes you are seeking.

On the day itself, a coach can facilitate, bringing new knowledge of methods and tools to get the best strategic thinking and decision making from the team.

Asking a Scaling up coach to facilitate your strategy session frees up the C-level to participate fully in the discussion. Rather than having to juggle between time keeper, facilitating discussions, managing logistics and contributing to the strategic decisions and discussions themselves.

If you would like some support preparing and facilitating your next strategy planning session, just reach out to me below. I am happy to help.


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