The 3 Primary Drivers of a Successful Strategic Leadership Event

Stacey Ashley Blog

The 3 Primary Drivers of a Successful Strategic Leadership Event

Are you wondering how to go ahead with a successful strategic event right now? Not sure whether it’s the right time? Unclear how to make it useful and ensure it delivers the outcomes you need?

‘I know I need to get my team together but I’m not sure how.’

‘I’m worried about how to make it work online.’

‘We need to update our strategy and plan.’

‘We need to get the leaders together to create a way forward for the business.’

‘We have already postponed our leadership team offsite because of the lockdown.’

‘Maybe we will just wait.’

This is what I’m hearing… hesitation, uncertainty, concern, confusion, and reluctance to go online with the important strategic events. Events like your Leadership Team Offsite, Strategic Planning and Team Building.

It’s not surprising that some people are challenged by the concept of creating a strategic space and time online. It’s like giving up your beloved VHS video library and replacing them with DVDs. It’s hard to let go.

There are a range of responses to the idea of taking historically physical face-to-face events into the contemporary digital world for a live online face-to-face event.

Planning Possibility Ladder

The real question is can you afford not to?

It’s risky to put off these essential strategic activities, to miss out on spending time in the strategic space to focus on your organisation’s future and develop your team’s capability.

What is the likely cost of this inaction?

‘The greatest danger in times of turbulence is not the turbulence; it is to act with yesterday’s logic.’

Peter Drucker

You can deliver a successful strategic leadership, team, or planning event live online. To help you take strategic action now, here are a few things to consider.

… And these ideas work for physical face-to-face events too.




Firstly, you need to create clarity about the why, what, how and who of your strategic activity.

Clarity of purpose:

  • Why should we have this event/activity?
  • What makes this activity important?
  • Why now?
  • What are the key outcomes you need and want from this event?
  • What are the triggers?
  • What is the impact if you don’t go ahead with the activity?
  • What is the benefit if you do?

Clarity of process:

  • How will the activity work from beginning to end?
  • When will this happen?
  • Which channels of delivery will you use? – both physical and online

Clarity of participation:

  • Who will participate? – team, leaders, customers, stakeholders, speakers, guests
  • Who will be needed to support and run the event?


So how do you get your strategic planning and leadership offsites to go ahead?

This is about gaining the engagement and endorsement for the activity. You need to establish the backing and the buy-in from the key stakeholders that this is an important and priority activity. And as such, is not subject to delay because of a change in delivery conditions eg. a snap lockdown event.

This part is essential. Create commitment to follow through on having your strategy offsite, whether it is a physical face-to-face event or an online face-to-face event.

When you have this commitment in place, you schedule your event knowing it is acknowledged  to be of key importance.

You might choose to have Plan A – perhaps a planned physical face-to-face activity. And also have a Plan B –  to switch to an alternative live online event if there are circumstances which prevent the event from being possible in a physical face-to-face setting. More complex, though possible.

Or you may choose to leverage a live online approach as your primary event delivery option.  You play the long game, using contemporary digital approaches to take your offsite online. Creating every opportunity for your event to proceed.



Have you got the capability to run this sort of event well?

It’s a good question. While most people now have experience operating in the digital world, how often have you attended an online meeting, training, or event that didn’t really deliver? Maybe it didn’t keep you engaged, maybe there was more trouble shooting than content and progress.

While many people have successfully managed to transition to the online environment, in my experience fewer people have managed to replace the presence of physical proximity with their presence and proficiency online.
Having the right capability and expertise is key to delivering an excellent online experience and achieving the important outcomes of your event.

Consider these questions:

  • What facilitation capability do you need to run a professional event?
  • What capability do you need to design the right agenda, develop the activities, collaboration, discussion, mastermind, and group activities?
  • Which technology will you use? Including your event platform, collaboration tools, resources, and so on.
  • What equipment do your participants need in order to comfortably participate and contribute to the event?
  • Consider the level of proficiency needed to use the technology and participate in the event. Is there any capability development requirement for your participants?
  • What kind of event planning capability do you need?
  • What about catering requirements and support, if any?

Some of these capabilities you will no doubt already have in your team and organisation. Some you may not. There is a big difference between running a one-hour zoom meeting and facilitating an engaging multi-session strategic collaboration event.

Understanding where you may need help is one of your key considerations. You may need to get an expert to facilitate and/or design your event, or to teach you how to do it proficiently.

The challenge right now is that after an optimistic start to 2021, some leaders are falling back into FREEZE and FLURRY type responses. Delaying decisions and action taking. Adopting a wait and see approach because of the ongoing uncertainty, in part caused by intermittent lockdowns and border restrictions. They are putting off key strategic activities.

These tactics do not create the best chance for you and your organisation to be future ready.

It is reasonably simple. In order for your organisation to have every chance to survive, in order for your people to know where to focus, you need to have your leadership offsite, your strategic planning and strategy day. And if you can’t have it offsite, you must bring it online.

Play the long game.

‘Innovation distinguishes between a leader and a follower.’

Steve Jobs

By considering and addressing the 3 key drivers of Clarity, Commitment, and Capability you will be positioned to execute an efficient and effective event.

The one essential thing that will give you every opportunity for a successful event…is that you go ahead with it.

I’d love to know your thoughts.

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