Beware the ‘When…Then’ trap
Digby Scott & Midjourney.com

Beware the ‘When…Then’ trap

“Expectation is the root of all heartache” - William Shakespeare

Many organisations I’m working with are going through brutal change processes. Cost cutting, redundancies, restructuring. It’s tough.

An Executive Team I was working with last week was talking about how they’re leading through it all. A common sentiment that kept bubbling up was “When we get to August then things will be better.” I discovered that this was one of the key messages they’d been using in the conversations and comms with their people.

That’s an example of what I call the ‘when…then’ trap.

As in, “When we’re there, then things will be better.”


The road to hell…

This message is well-intentioned. As leaders, we can feel the pressure and responsibility to relieve our people of the burden that they’re going through. It’s not their fault, right? We’re ‘doing change to them’. We use ‘when…then’ to show people there’s a light at the end of the tunnel. Because, as Napoleon Bonaparte once said, ‘Leaders are dealers in hope’. Right?

Well, yes. However, using a ‘when…then’ leadership strategy is risky.

When the ‘future’ becomes the ‘present’, it’s usually not what we predicted. No one can predict the future. When we rely on ‘when…then’ to keep our people focused and engaged, we’re at risk of creating an expectation gap. A gap between a future that we expect, and the reality of what actually happens.

The problem with this approach is:

  • We’re setting up expectations that we don’t have much control over. If the new reality doesn’t meet expectations, we’re at risk of breeding further disappointment and frustration
  • Change has a long tail: just because some reorg has happened on paper, the real work of change is ongoing and never ‘done’
  • We’re robbing people of the opportunity to sustainably learn and grow through adversity.


The stories we tell ourselves

Why do we take this approach? The drivers behind a ‘when…then’ approach can be multiple:

  • The need to keep people happy (don’t worry, let me tell you how good it’s going to be)
  • The need to be the rescuer (don’t worry, I’ve got you!)
  • The need to be the hero (don’t worry, I’ve got this!)

Underlying these drivers is a common story: 

I, as the leader, am responsible for making bad things go away. 

That’s a heavy burden to carry.

I reckon there’s a better story we can tell ourselves:

I, as the leader, am responsible for helping people make good choices in uncertainty. 

This story has a subtly different flavour. One that keeps responsibility where it needs to be. While still dealing in hope.


See. Imagine. Do

With every change comes opportunity. Our work as leaders is to invite people to play their part in grasping the opportunities that exist. It might not be easy. But it keeps it real. And people want real.

This is about working together with people to see, imagine and do:

  • See: Give people the opportunity to be grounded in the reality of now. Facilitate conversations that help to explain what’s changing, and what’s not. Talk about what we can’t do anymore, what we still can do, and the opportunities that exist to try new things. The Four Doors of Change is a great tool to help with this.

  • Imagine: Be what negotiation expert William Ury calls a ‘possibilist’. Put more emphasis on possibilities rather than problems. Conductor and educator Ben Zander tells the story of two shoe salesmen visiting a developing country. One sends a message back to head office. “The situation is hopeless. No one has any shoes.” The other writes back “What an amazing opportunity! No one has any shoes!”

  • Do: Focus on helping people clearly see the choices they have and how they can make them. Show them how they can contribute to creating a better future, and what resources are available to help them take action. The clearer people are, the more agency they will feel.(Thanks to Nick McKissack from HRNZ for this prompt)

When leading through change, beware the ‘when…then’ trap. Instead, try using the ‘see, imagine, do’ approach to help everyone come through it stronger. 

Because we bring out the best of our humanity when we’re invited to shape the future, not merely to be shaped by it.


For more like this, check out:

See. Imagine. Do. Three Practices for Effective Leadership

Are You a Responsibility Hoarder?

This Too Will Pass. But How Will You Experience It?

Caroline Dewe

CEO and Founder at Alphero

5mo

Hey Digs! Good points. We’ve added a new mantra to Alphero the past 18 months: A lot of bits add up to a lot. We broke down a boatload of small actions that each person or team could take to contribute to shifting the dial in a challenging market and asked everyone to do their part. We’re also facing into the chaos versus waiting it out. It’s really worked for us. Doesn’t put the load on any one part of the business. And empowers the team to contribute.

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This nails it Digby. I'm witnessing leaders being unable to tell people the hard truth at the moment. It comes from a good place and makes people feel good at the time, but it isn't great for people who need to plan for the longer term. Thanks for the post!

Sue Hope

Consultant | Director | Mentor | Coach | Volunteer

5mo

Thanks Digby as always nailing it and providing great advice to use straight away!

Matthew Needham FCPA

Strategic Leader | Speaker | Author | Mentor | Accelerating Organisational Performance through Culture, Change & Strategic Prioritisation | Award-Winning CFO

5mo

This essentially describes what Vice Admiral Stockdale observed in Vietnamese prison camps and became known as the Stockdale Paradox. Where you must maintain unwavering faith that you can and will prevail in the end, regardless of the difficulties, and at the same time, have the discipline to confront the most brutal facts of your current reality, whatever they might be.

Danni Ermilova Williams

Impact Coach | Biz Consultant | HR + Change Specialist | Disruptor of the status quo | CMHRNZ | MInstD | ICF Member | HRNZ Board of Directors | HRNZ HR Professional of the Year 22 | Ask about people, work + change

5mo

I love your authentic obswrvation and call out there D. Perhaps even a bit of parent-child in there... Either way a power-over model rather than empowerment approach doesn’t bode well for anyone. Too many curious thoughts to write here on this, but thanks for opening it up.

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