Asking tough questions.

Strategic Listening

Listening is the heart of good communication and strategic conversations. Asking good questions is an important part of listening but first you need to get the distractions out of the way.

Asking tough questions.
In the TV show SUITS, the main characters are masters of asking tough questions.

Listening to someone is a real gift because it allows them to clarify their thinking and you can then reflect back their thinking with even more clarity.

Strategic Listening: 8 things I learnt the hard way

1. Get out of the office

Some of the best strategic conversations that I’ve had with clients have been in a cafe, on the plane home after a workshop, or at a pub. If you can’t get the CEO out of the office, try for early mornings or late at the end of the day when everything else has been taken care of. The aim is for you and the other person to be one hundred percent in the room. No Blackberries in a strategic conversation.

If you can’t get a proper one-on-one then at least offer to walk the client to the door after a meeting. The chit-chat on the way down to the front door can be the most important part of a meeting.

2. No props needed

Early on in my career, I used to use a whiteboard or an A3 pad to co-create the notes of a one-on-one meeting. This still has a place, but such a meeting is really a mini-workshop, not a strategic conversation. Props direct the eye and control the room in a way that stifles honest conversation.

A whiteboard marker can be just like the talking stick in The Lord of the Flies. Standing at the whiteboard (while the client sits down) changes the centre of gravity in the room. You want to be eye to eye with the CEO. That means a Moleskine notebook on the table between you (at most).

3. Triangulate by trying different angles

When I was a young law student, we were trained to define things by subtraction. To mark out what something is, by carving away what it is not. This is an incredibly powerful way of attacking strategic consulting problems. If you can’t figure out what the brand essence of a company is, just keep testing different hypotheses until you know what it isn’t. This requires a willingness to ask stupid (or hard) questions.

The most important part of definition by subtraction is to try your questions from lots of angles. This is like defining a solution by sonar. You take a reading from one place, then move to another place and ping the solution again. Mathematically, triangulation means that after three readings you should have an idea where something is. I’ve found that with navigating ideas (as opposed to real navigation) you need a lot more than three pings to triangulate a problem.

In practice, triangulation in conversation looks like defining a brand by ping pong because you’re asking the client lots of questions, taking their answers, calibrating them and then asking more questions. It requires patience, but it’s a great way to pin down a wicked problem.

4. Don’t be afraid to ask why

A neat tool for quickly deepening a conversation is the “Five Whys” from Japanese Lean Manufacturing. The trick is to ask “Why?” five times about a problem to peel away successive layers of causality and intent. Try it out at home: Ask yourself why you love your job (then ask “Why?” five times more) and you can probably get to some pretty interesting stuff.

Consultants trained in neurolinguistic programming often ask ‘Why is that important to you?’ when doing values elicitation with a client. Asking why is a fast way to get to the real heart of what’s going on in a situation. But it’s not a safe or easy question to ask.

5. Use leading questions to narrow the focus

As a lawyer, you never ask a question in the courtroom that you don’t already know the answer to. The equivalent in business strategy is to make sure that you understand the client’s business and that you can maintain client confidence by keeping the process on track. The risk is that this blinkers you to the simple solutions and makes you less curious about what is really going on. Prior knowledge can be a real curse. One way through this is to be clear when to use leading questions and when to avoid them.

You want to lead the client when converging on a solution based on robust research. Such as getting management buy-in on a plan based on a whole company consultation. You want to avoid leading questions when doing the initial audit and discovery phases of the project. Keeping an open mind the whole time is the key, even when leading the witness.

6. Use a Strawman suggestion as a starting point

The strawman is like the scarecrow from The Wizard of Oz. It’s not a finished idea but you can put it out there and see how people react. I think of a strawman as a minimum viable idea. A strawman is not the same as a leading question. You can propose a working idea of the brand essence to get input but you can still be open about what the reaction might be.

A strawman is a powerful part of a strategic conversation because you can get an immediate reaction and it’s a great way to triangulate a solution. Rapid prototyping and creative thinking thrive on creating lots of bad ideas, so that the good ones can survive.

7. Practise the art of not knowing

The other side of leading questions and strawmanning, is to practise not knowing. This is the Zen Mind, Beginners Mind approach to strategy. Like asking why, the art of “not knowing” is all about being curious. If you find yourself saying “I know what the client is going to say next”, instead, try pretending that you don’t really know.

Pretending to not know everything is a great way to get a better quality conversation because you will start asking more probing questions. The great thing about this type of conversation is that you can stop relitaging the past and talk about how the client wants the future to look. Letting go of assumptions and preconceptions is a great way to uncover a company vision.

8. Hang out in the uncomfortableness

If you are going to ask the CEO private and personal questions about their goals and aspirations, you are going to have to create a safe space. But you’re also going to have to be ok with a few moments of uncomfortable silence. If you’re going to call them out on areas where they have let themselves down, you need to be comfortable having uncomfortable conversations. That’s how real change is made, by being willing to say or ask what the day-to-day staff are unable to say. A strategic conversation can make a real difference, if you are tough enough to ask the important questions.