Is everybody ‘perfectly aligned’? Well, think again!
The Top 5 Leadership Blind Spots Revealed: Have you Got Any?
Is everybody ‘perfectly aligned’? Well, think again!
The Top 5 Leadership Blind Spots Revealed: Have you Got Any?
Show all

A ‘Killer Question’ for Your Tech Project Kickoff

Digital transformation has moved up the corporation's agenda. It also had a new leader. With a kickoff meeting on the calendar, the leader starts to wonder how to get things off to a strong start.

Slide presentations weren't going to be enough. With engagement as the aim, the leader discovers the power of the killer question: ‘What does success look like?'.

The Digital Transformation Kick-off

The meeting invitations for the transformation project kickoff were sent out early. Yet, it wasn't until the week before, during a coaching session, that the busy project leader paused to plan the kickoff agenda

‘How important is the meeting?' asked the coach innocently. ‘Very important', replied the leader, citing many reasons:

  • ‘We are setting out on the new stage of our digital journey’ he added. 
  • ‘This meeting was to be the first time that all those involved in digital projects across the national organization would be coming together’. 
  • ‘This is also the first time that the sponsoring senior executive will meet all the team members, so it's essential to create a good first impression. 
  • Also, this is my first meeting as the team leader, the first meeting where the previous leader won’t be present. So, it is a new beginning.

Because the meeting is so important, I plan for its success. ‘As an organization, we often don't do meetings very well', the leader reflected. ‘I don't want us to fall into bad habits, ‘ he added.

Planning for Kick-off Success

‘What does success look like for the meeting?' asked the coach. The leader's answers to this question were clear.

‘Success is that people are energized and engaged', replied the leader. ‘It is not a set of slide presentations or a few people doing all the talking. Also, I want things to get off to a good start – I want this meeting to help set us up for success,' he added.

‘Moreover, I don't want us to get lost in the weeds, but to stay high – to be more strategic,' said the leader. ‘We could quickly get caught up in the detail of a specific project, idea or proposal – that would be a mistake', he concluded.

This was music to the coach's ears. He couldn't help remembering the first meeting (chaired by the leader) he had attended. To his amazement, the leader had dominated the meeting – talking for about 75% of the time. The rest of the people attending that meeting – all bright, experienced and intelligent executives – stayed silent.

But that was eight months ago, and the leader had taken on board the coach's honest (and challenging) feedback. The kickoff would be an opportunity to see the leader's new, more engaging style.

Setting the Agenda

After a brief pause, the coach continued to probe regarding the kickoff, asking: What are the topics or items on the agenda?' ‘Here is what I had in mind', replied the project leader, setting forth the following details:

– Project status – Project triangle (scope, time, budget, etc.)

– Project Goals and Deliverables

– Business & Stakeholder Needs

– KSFs, risks & dependencies

– Project team – ways of working

Having shared the list of agenda items, the leader paused momentarily and then commented: ‘I am worried that this might be too long for a two-hour meeting'.

‘I think you are right — It is a long list.’ replied the coach.  

‘What if the points on the agenda were re-worded as questions?' asked the coach. Also, what if we narrowed the list? For example, a great question for the kickoff might be: “What does success look like?” More specifically, what does success look like regarding our digital transformation over the next 12 months?

Why is it a ‘Killer Question'?

‘That is interesting', replied the leader in reflective mode. But hasn't success been defined in the strategy? Why don't I just put up the slide on project goals and deliverables?' he added.

‘Well, you certainly could let the slide do the talking', responded the coach. ‘But it won't generate the same level of ownership, engagement or buy-in'. ‘Reading from the slide probably won't get people excited', he added.

‘When you ask people what success looks like, you evoke their imagination and emotions – you connect to their passion and motivation too,' continued the coach. ‘The definition may be the same as defined in your project plan, but by asking, you get people to talk about success in their own words and as it relates to their work', he added.

‘We call this a ‘killer question' because it connects not just with the ‘How?' of what we're trying to do, but also the ‘Why?'. That is important because, as they say: ‘the why is big enough, people will find the how,' added the coach. ‘This is the application of that seminal principle: begin with the end in mind,' he concluded.

‘I like it', replied the project leader, adding: ‘What could be more motivational than to discuss what success looks like? I think it will reveal much about the project and the team,' he added. ‘Let's put that as the number one item on the agenda', he decided.

‘What does success like' is a key question in the first mile of any project or initiative. It is the 2nd step on the 5 stage journey from strategy to success (shown here). Yet, it should be asked at all stages.

Different Perspectives on Success

With 11 people in the kickoff, the killer success question revealed 11 perspectives on success. Rather than being a source of frustration, it generated excitement and engagement. Many of those attending suggested that this was one of the best project meetings ever had. 

The various perspectives on success are summarized below. As you read them, you will see that many of them overlap. There are key repeating themes, particularly balancing the need to deliver in the short term while shaping the longer-term digital vision. Clearly, more conversations like this would be required before a shared definition of success would emerge.

  1. ‘We have been rolling along in terms of a project or solution here. That has worked to date, but isn't it now time to put an overall framework, strategy and structure in place guided by a vision of how digital transformation will shape the future of the organization?
  2. ‘We can't be seen to be left behind playing catch up in what is happening in other parts of the organization globally. Success starts by looking for a role model. If the role model isn't in our organization, maybe it is within a competitor'.
  3. ‘For next year, I believe we should be focusing on Quick wins. We should be tackling the most obvious pain points, frustrations and inefficiencies that exist within the organization. Demonstrating some quick-wins or progress in areas that matter to key stakeholders is key. If we do that, we can give people a sense of what is possible and be assured of organizational backing into the longer term.'
  4. ‘I believe we should start small and build incrementally. Otherwise, we could scare people. This is a long-established organization that doesn't do things fast. Most important of all, we need to avoid a false start. We must ensure people are aligned and bought into what we are doing. Otherwise, we will have to battle with resistance to change.
  5. ‘We have an assortment of systems that hold information in silos and require manual intervention to generate reports or manage transactions. Tackling this has to be the biggest area of potential win for the organization in terms of digital. It is a no-brainer.'
  6. ‘This may sound strange, but success next year means doing everything correctly. The digital initiative is beginning to get attention across the organization; we must manage expectations and communicate clearly with all the stakeholders. We must be careful not to overpromise and under-deliver.
  7. ‘Today, I don't think we can answer questions such as ‘What is the vision?' or ‘What is the overall strategy?' I think that will take time. But, by the end of the year, having a clear vision and strategy for digital should be the goal. Otherwise, people might say we are simply tinkering at the edges or making it up as we go along. 
  8. ‘Before we set out, don't we need to know where we're heading? Don't we need to know what the vision is? For me, success means that we are clear on where we are going and how we will get there. We have a vision and a strategy. Putting this in place has to be key to success over the next 6 to 12 months.'
  9. ‘The business ‘why' must be clear and compelling. Today, we are not sure what that is. Yes, we can deliver efficiencies, but is cutting headcount an option given the organization's history and ethos?
  10. ‘Coming from a marketing background, I see success through the lens of the customer and supply chain partners. How will digital enable us to serve our customers and partners better? Where the points of frustration – the delays, holdups and bottlenecks in terms of how they interact with us and with our systems? Isn’t that where we should focus?’ 
  11. ‘We have world-class plant and equipment.  We also have the latest and the best in term of ERP and other related systems.  So, shouldn’t we be aiming for the same standard in terms of our use of digital technologies too?



SOLUTIONS & SERVICES: Here are some of the ways that our research & insights are put to work by our clients:





Comments are closed.