The Blog.

The “When-Then” Strategy

13 Jun 2016 | Tips, tools, tricks

Want to make something a habit but hate the idea of scheduling? If so, the “when-then” strategy could be for you.

In many of my workshops and coaching sessions, people love the idea of breaking bad habits like constantly checking emails or going to bed late, or building good habits like Inbox Zero, weekly reviews and taking breaks.

Taking these ideas into action, however, can prove trickier.

“I find myself in need of a break so I quickly check my emails for some light relief. Two hours later, I’m still there.”

“I’d really love to get more sleep, but when evening comes, I start thinking of all the things I still need to do and end up ploughing through.”

“I’d probably come up with some much better solutions if I just give myself some time to think, but it’s really difficult to stop firefighting and work out a plan.”

These are all comments from people I’ve worked with, who have found the annoying truth, that building habits is a whole lot harder than just knowing what to do.

For some people, scheduling can be a great way of making the decision once and just following through, instead of relying on willpower to make the decision over and over again. For example, scheduling set times to process email or set times to go to bed, and set times for planning means that they don’t have to constantly evaluate “what should I be doing now?” throughout the day and run the risk or decision fatigue.

But scheduling doesn’t work for everyone.

For some people (myself included) too much scheduling can feel overly restrictive.

Personally, I can set aside a block of time in my diary to work on something, but telling myself I’m going to do the same thing every day/week at set times, gets my brain rebelling like a teenager with a rather pathetic but very powerful “but I don’t feel like it!”

Plus there’s the added complication that the nature of my work doesn’t always lend itself to structured days and routines. Sometimes my day starts at 9.30 after walking the kids to school. Sometimes it starts with a 7am email session in a hotel room before diving into a full day workshop. Some weeks I’m based at my kitchen table, other weeks I’m trekking across the county.

Cue the “When-Then” Strategy

All credit for the name goes to Caroline Webb – I didn’t realise I was doing this until I read it in her book “How to Have a Good Day”.

In this case, the “when” isn’t a set time, but a trigger, such as “When I wake up…” or “when I feel tired…” or “when I’ve finished x…”

So instead of “I will only look at my emails at 9, 12, and 4″ (which works for some people but not all), your “when-then” strategy could be:

“When I have finished this piece of work, then I will look at my emails.”

“When I log in in the morning, I will write my day’s to-do list first, then I will check email.”

“When I open my inbox, then I will start a timer for 20 minutes, and when that rings, then I will close Outlook and move on.”

“When I feel like I need a break, then I will give myself a proper break and walk away from my desk instead of checking emails.”

Why does this work?

In “The Power of Habit” Charles Duhigg’s research found that a trigger is the most powerful part of a habit. Knowing what triggers a bad habit can help you identify and replace it with a different action. Telling yourself “I’m not going to check my emails” is about as useful as a smoker saying “I’m not going to smoke” and hoping for the best. Identifying the triggers however, can help you to identify the potential triggers or temptation, and deciding on a specific action you want to take instead.

When I gave up smoking many years ago, I identified lunch time as a trigger, so when I went for lunch, I’d ask a friend or colleague to join me. Instead of smoking I’d ask them to keep me talking, so there was something else for my mouth to do.

By pairing up certain triggers and habits, the more we repeat them, the more automatic they become. It always amuses me that my bedtime habit of going to the bathroom, taking out my contact lenses and brushing my teeth are so wired together that, on the odd day when I take my lenses out early, I can find myself brushing my teeth in the middle of the day, or putting my lenses back in before going to bed!

What else could you use this for?

You can also use a “when-then” strategy for building habits that are more situation-specific rather than time-bound, for example:

“When my brain starts churning with ‘to-do’s in the evening, then I’ll go into boss mode to review and make a plan for tomorrow, rather than go into worker mode for a night shift.”

“When I feel like I’m firefighting, then I’m going to take a glass of water, a pen, and a piece of paper to a quiet spot, write “don’t panic” at the top”, “take control” at the bottom and work out my steps to get from the top of the page to the bottom (thanks to a workshop delegate who shared this one)

“When I’ve lost focus, then I’ll take a break rather than try and plod on through”

“When I find myself procrastinating, then I’ll message Grace to hold me accountable.”

“When I can’t give a wholehearted yes, then I’m going to make it a clear no, and here’s what I’m going to say…”

“When imposter syndrome kicks in, then I’ll revisit my Champagne Moments folder.”

“When I catch myself checking my phone, I’m going to say to myself “Nothing to see here. Move along.”

“When I’m feeling overwhelmed with responsibility, then I’ll ask myself what will help me to be more response-able

You get the picture. So what about you? Where could you use a “when-then” strategy? Drop me a line in the comments box below – I’d love to know your thoughts.


  1. Richard Tubb

    Grace – I love this idea. Thanks for sharing and the recommendation for the “How to have a good day” book by Caroline Webb. I’m going to give both a go!

    • Grace Marshall

      Excellent Richard – let us know how you get on!

Image if author Grace Marshall

About Grace

I coach, train, write and speak on productivity. I help people adopt new ways of working and thinking about their work to replace stress, overwhelm and frustration with success, sanity and satisfaction.

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