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Insight Planning: Putting “Listening” to Work

Mini Mind Maps put listening to work

Push­ing toward a rel­e­vant truth is the clear­est path­way to hearts and minds. If you can deliv­er on rel­e­vant truths con­sis­tent­ly, you’ll find that rela­tion­ships fol­low. But why is it so hard to find these truths? We’re gonna talk about why it’s hard, and then illus­trate the process using a sim­ple exam­ple.

Insight Planning Tells You What They Need to Hear

Most mes­sages get caught up in the noise. How do we get cus­tomer insights that tell us what we should be ask­ing? The answer is sim­ple; but if you don’t know what you’re doing, the process is hard.

Put sim­ply, insight plan­ning is ask­ing the cus­tomer for the deeper/real rea­son they buy, and so you can cre­ate adver­tis­ing that tells it right back to them. And if done right, it can seem like cheat­ing. Unfor­tu­nate­ly, peo­ple don’t know how to listen…or they don’t think they do.

In busi­ness, it’s easy to think the cus­tomer is a machine. On one lev­el, we know they’re peo­ple. But we’re in a hur­ry, and we need to do more with less. So instead of con­nect­ing with peo­ple, we look for tricks and short­cuts. And instead of doing more with less, we end up doing even less…with less.

Insight Planning is Simple, but Hard

Why don’t more com­pa­nies con­duct insight plan­ning? Because it’s not easy to mea­sure, and every­one wants results right now. So the only peo­ple who do it are those who want a deep­er con­nec­tion with their audi­ence. You know, peo­ple who are will­ing to do the hard work of rela­tion­ship build­ing.

In oth­er words, you have to

  •        Real­ly care what your cus­tomers want
  •        Believe there’s some­thing about them you don’t under­stand
  •        Have the con­fi­dence you can get that infor­ma­tion if you have the right kind of con­ver­sa­tion.

Example Workflow

But instead of me explain­ing the process, let me jump right to what it looks like. Let’s use a tac­ti­cal train­ing com­pa­ny in our exam­ple. They train peo­ple on how to use firearms effec­tive­ly and safe­ly. Take a minute to trans­late these ques­tions into your busi­ness.

First, some advice. The key to inter­view­ing is to do one-on-one inter­views, make them feel relaxed, don’t inter­rupt, get them talk­ing and slow down the rhythm. You want to go deep­er into the ques­tions they seem inter­est­ed in answer­ing. You know, exact­ly like you’re talk­ing to a friend who real­ly needs a lis­ten­ing ear.

Insight Planning by Role

Here’s who you talk to and the kinds of ques­tions you’ll ask.

Sales. You talk to sales because they’re close to the cus­tomer and often know what turns peo­ple on to buy. They also know what top­ics they try to avoid with cus­tomers because they’re embar­rassed. But be care­ful, sales­peo­ple aren’t always the best lis­ten­ers, and they have blind spots too. Often, they’re blind to cus­tomer objec­tions, depend­ing on their per­son­al­i­ty.

  • What is it that peo­ple don’t under­stand about the ser­vice?
  • What’s the hard­est idea to sell? Why?
  • How are peo­ple using the prod­uct? Why?
  • What do they love about it?
  • What kinds of objec­tions are peo­ple bring­ing up most? Why do you think that is?
  • Why do peo­ple go to a com­pet­i­tive prod­uct (even if it’s choos­ing to do noth­ing)?

Cus­tomer ser­vice. You talk to cus­tomer ser­vice because they’re deal­ing with repeat issues and can tell you the gen­er­al feel­ing of cus­tomers after the sale. But be care­ful, since they’re more con­cerned with min­i­miz­ing prob­lems than cre­at­ing oppor­tu­ni­ties.

  • What are the biggest com­plaints? Why?
  • What are the things you’re most proud to tell peo­ple? Why?
  • What are the things about the prod­uct that seem hard­est for cus­tomers to under­stand?

Cus­tomers. Talk to cus­tomers because, locked with­in them, they have all the answers you’ll ever need about what will make them buy. But don’t expect them to inno­vate for you. Often, they don’t know what you’re capa­ble of doing, so they won’t be able to give you ideas for “how to serve them bet­ter.” Instead, you’re look­ing for them to tell you about their lives. Then you come up with things you’re able to to do to make things bet­ter. So take your time.

  • What’s your moti­va­tion to par­tic­i­pate in train­ing? Tell me more about that.
  • What’s your biggest fear that train­ing would pre­vent? What’s the gap in train­ing for you? In oth­er words, where’s the remain­ing inse­cu­ri­ty that you don’t think train­ing could pro­vide? [Here, you’re guid­ing them to an insight that your com­pe­ti­tion doesn’t thinks is there.] Tell me more about that.

Schedule of Tasks

Here’s how insight plan­ning plays out for our fic­tion­al tac­ti­cal train­ing com­pa­ny.


  1. Write a dis­cus­sion guide.
    • For sales and inter­nal.
    • For cus­tomers.
  2. Sched­ule 6 meet­ings:
    • 2 with sales on Tues­day.
    • 2 with cus­tomer ser­vice on Wednes­day.
    • 2 with cus­tomers on Thurs­day.


  1. Have your first 2 inter­views with sales.
  2. Build your skills with your sales and inter­nal folks. See if you can get them talk­ing about their jobs and rela­tion­ships with cus­tomers.
  3. Edit the dis­cus­sion guides as much as you see fit.


  1. Con­duct 2 inter­views with cus­tomer ser­vice.
  2. Record/capture your insights from sales and cus­tomer ser­vice in clear­ly edit­ed for­mat, with quotes.
  3. Cre­ate a work­ing hypoth­e­sis for the kinds of things cus­tomers would be inter­est­ed in talk­ing about and adjust your dis­cus­sion guide for tomor­row.


  1. Con­duct your 2 cus­tomer inter­views, cre­at­ing a relaxed, gen­er­ous envi­ron­ment where you ease into the con­ver­sa­tion and free them to speak, unjudged.
  2. After both are over, cap­ture insights and quotes and build a 2‑page sum­ma­ry of only the most clear insights. This is just a draft.


  1. Edit your insights. Write well and be as clear and blunt as pos­si­ble.
  2. Share those insights with your team or part­ners and deter­mine 3 ways that the insights should change the way we do things.

Pro Tips

  • This exer­cise is ide­al­ly done with 12 cus­tomers by a skilled inter­view­er. But most busi­ness­es would ben­e­fit mas­sive­ly from just hav­ing even just a few con­ver­sa­tions, like in the above exam­ple.
  • Keep the con­ver­sa­tion going. Let this spur an ongo­ing effort to block off time to think strate­gi­cal­ly, not just putting out fires, so you can build a long-term effort. Let me know if you need sug­ges­tions.
  • Record video of the cus­tomer con­ver­sa­tions if you can. There’s noth­ing quite as con­vinc­ing as hav­ing your cus­tomers’ voic­es and facial expres­sions telling the sto­ry, espe­cial­ly if you need to con­vince oth­ers of your results.
  • Snow­ball: Ask the inter­vie­wees who else you should be talk­ing to.

Now that I’ve told you how to do it, don’t fol­low this process. Make it your own. Do it faster or slow­er. Mix up the num­bers.

This is Just the First Step

If you can cre­ate a tra­di­tion of lis­ten­ing well, with the plans and process­es to put the insights to work, you won’t be a fake. Instead, you’ll be putting your mon­ey where your mouth is, cre­at­ing val­ue for cus­tomers as a hum­ble, lis­ten­ing ser­vant-leader. And you’ll grow rela­tion­ships as peo­ple start to love you for it.

Care to dis­cuss?