How to Help your Managers Have Insightful Career Developments Conversations With Employees

In previous blogs, mentioned the importance of making that shift from boss to coach. And how the role of a manager is more effective when coaching staff rather than managing them.

We also covered the intricate personalities of how to coach people where they are based on their personalities, their strengths and who they are so they feel they are getting the most value by working at our companies.

Now, we are going to cover the culture of development and unpack the famous one-on-one — the coaching conversations your managers should be having with every team member.

In this blog, you will also find a career framework to have the most effective one-on-ones.

What is a Culture of Development?

Your goal as a leader of an organization is to create more leaders. To accelerate those skillsets and empower other people.

The problem is that most leaders are stuck on leadership requiring positional authority. Members of your organization think that they must be a manager or a director in order to lead.

The truth is that leadership is ultimately about the development of other people.

Therefore we must create a culture of development to develop more leaders in our organization.

Shift from positional leadership to a focus on the development of your team.

To begin with, creating a culture of high development requires more than completing an annual employee survey and then leaving managers on their own - hoping they will learn something from the survey results that will change how they manage. You need to take a closer look at how critical engagement elements align with your performance management and human capital strategies.

High-development companies have a clear purpose behind their strategy for employees. They know the specific behaviours they are trying to achieve and why those behaviours matter for success. We have to get clear on which behaviours we want to coach for.

Before continuing, watch this video for my 3 secret tips to achieve peak team performance.

Laws of Learning

John Wooden was a basketball coach at the University of California, Los Angeles. He had led UCLA to nine national championships in ten years. Even ESPN named him the greatest coach of all time in any sport.

One of Wooden's most frequent forms of teaching was this three-part instruction where he modeled the right way to do something, the wrong way, and then he remodeled again the right way.

What looked like this flow of improvised drills and coaching is actually something that was extremely structured and focused.

He was making it easier for the players to know what to change and building on learning circuits by seeing and fixing errors.

He had his own laws of learning. He would teach in chunks, or what he called, the whole part method.

This is a big part of Daniel Coyle's research, it shows how the whole part method, the chunking method of learning, is extremely effective and the most effective way to learn.

This law of learning has five components: explanation, demonstration, imitation, correction and repetition.

Quite simple, yet powerful in its approach for teaching, learning and coaching.

"Don't look for the big quick improvement. Seek the small improvement one day at a time. That's the only way it happens, and when it happens, it lasts." — John Wooden.

Repetition is key to learning.

What we learn from John Wooden here is that we must think of coaching our direct reports and our team with these short bits. These constant short bursts of feedback. These constant short bursts of accountability. These constant short bursts of demonstration and imitation and repetition of new ways.

Speaking of constant conversations, below are five coaching conversations your managers should be having with their employees.

The Five Coaching Conversations

Coaching conversations are the accumulation of everything we’ve been learning thus far.

A coaching conversation must create psychological safety. It has to make someone feel like they belong, has to include vulnerability. It must be individualized to the person through their own personality, it must empower the coachee with more clarity on their roles and goals, while still keeping them in the decision-making seat. It must offer high energy and engagement when you're communicating. It has to include radically candid praise and feedback.

Without any intention Wooden (the coach we referred to above) used Gallups 5 Coaching conversations:

1. Role and Relationship Orientation

2. Quick Connect

3. Check-In

4. Development Coaching

5. Progress Review

We break down each coaching conversation on our blog, The Coach Approach: How to go from Boss to Leader.

But how do you prepare to have these conversations? Well, we use a framework.

Keep reading to understand what we mean 👀

Effective One-On-Ones

The most effective one-on-one are the ones we prepare for, that we have plans for, and that we actually have spent time thinking about.

But we don't always have that time to plan.

At Unicorn Labs, we’ve come up with this set of questions to help you coach during your one-on-ones rather than what you're probably used to which is giving all the answers.

Let's dive into this a little more.

Giving advice is easy. People like to hear it and they think that your advice is good. However, the real value of coaching lies in asking questions instead of giving advice.

Asking questions can be a little awkward. It’s important to ask them if you want to improve your employee’s performance, but it may feel like they’re not very helpful at times.

Advice is overrated. I can tell you something, and it’s got a limited chance of making its way into your brain’s hippocampus, the region that encodes memory. If I can ask you a question and you generate the answer yourself, the odds

Questions make conversations slower. It’s EASIER  to be in control of the conversation rather than let it take its own course. Asking questions means you’re no longer in control, and that can lead to awkward situations.

Now that we understand the values in question. Here are seven types of questions to get your managers have insightful career development conversations with staff.

The Seven Questions

Here are a set of seven questions to help your managers navigate through conversations:

1. The Kickstart Question 🦵🏼

An almost fail-safe way to start a chat that quickly turns into a real conversation is the question “What’s on your mind?” Because it is open, it invites people to get to the heart of the matter and share what’s most important to them. It is a question that says “let’s talk about the thing that matters most.

Coaching for Performance versus Coaching for Development

Coaching for performance is about addressing and fixing a specific problem or challenge. It is putting out the fire or building up the fire - it is everyday stuff, important and necessary.

  • Addressing and fixing a specific problem
  • Putting out the fire or building up the fire
  • Everyday stuff, important, necessary

Coaching for Development

Coaching for development is about turning the focus from the issue to the person dealing with the issue, the person who is managing the fire. This conversation is rare and is significantly more powerful.

  • Turning the focus from the issue to the person dealing with it
  • Significantly more powerful (and rare) than coaching for performance

The 3P Model

The 3P model is a framework for choosing what to focus on in a coaching conversation – for deciding which aspect of a challenge might be at the heart of a difficulty that the person is working through.

The 3Ps refer to Projects, People and Patterns.

The Project side refers to challenges around the actual content.

The People side refers to issues with team members, colleagues, customers or clients.

The Patterns refers to if there is a way that you are getting in your own way and not showing up in the best possible way, where should we start.

Asking the Kickstart question works as a little pressure release valve and helps make explicit something that might be unduly influencing the way you work.

Projects People Patterns
- What projects do you need to abandon or postpone?
- What meetings will you no longer attend?
- What resources do you need to divert to the Yes?
- What expectations do you need to manage?
- What relationships will you let wither?
- What habits do you need to break?
- What old stories or dated ambitions do you need to update?
- What beliefs about yourself do you need to

2. The AWE Question 😱

“And What Else” – a seemingly innocuous question – creates more wisdom, more insights, more self-awareness and more possibilities out of thin air. It is the quickest and easiest way to uncover and create new possibilities.

Asking “And What Else” – will lead to more options and often better options. Better options lead to better decisions and better decisions lead to better success.

It is the simplest way to stay lazy and stay curious.

Managers could ask this question at least three times — till the coachee says “there is nothing else” — then, move on to the next question. If you have got 3-5 answers to the question – “What else” – you have made good progress.

Why it’s the best question to ask

This is considered to be the best question because of three reasons:

  1. Uncover and create new possibilities more options can lead to better decisions
  2. You reign yourself in
  3. You buy yourself more time

We all have a deeply ingrained habit of jumping into the advice-giver role when presented with a problem. Giving advice feels more comfortable than the ambiguity of asking a question. This urge is what Michael Bungay Stainer calls the advice monster.

"If this were a haiku rather than a book, it would read:
Tell less and ask more.
Your advice is not as good
As you think it is." — Michael Bungay Stanier.

4 Tips for Asking The AWE Question

  1. Stay Curious, Stay Genuine
  2. Ask it one more time
  3. Recognize Success
  4. Move on when it’s time  - is there anything else?

3. The Focus Question 🧐

The focus question — “what is the real challenge here for you?” — this is the question that will help slow down the rush to action. So, you spend time solving the real problem and not the first problem.

Some managers try to solve problems as soon as they arise. Instead of doing this, help people quickly figure out their own paths.

This question helps because the way people first characterize a problem often has nothing to do with the underlying issue.

This comes with three sets of questions to bring out different perspectives:

1. What’s the challenge?

Curiosity is taking you in the right direction, but phrased like this the question is too vague. It would most likely generate either an obvious answer or a somewhat abstract answer – neither of which is helpful.

2. What’s the real challenge here?

implied here is that there are a number of challenges to choose from – you would have to find one that matters the most. Phrases like that will make them slow down and think more deeply.

3. What’s the real challenge here for you?

Pins the question to the person you are talking to. It keeps the question personal and makes the person you are talking to wrestle with her struggle and what she needs to figure out.

If the person talks of many challenges – asking the question “if you had to pick up one of these to focus on, which one would be the real challenge for you?” would do the trick.

You’ve likely already mastered the fake question, a subtle art of giving advice and nudging a person along your preferred direction.

👉 “Have you thought of…?”

👉 “What about…?”

👉 “Did you consider…?”

In a focused conversation, it is better not to ask “Why” for two reasons:

  1. You put them on the defensive. Get the tone wrong – the why could come across as “What the hell were you thinking?”. Why feels accusatory from when we were all children.
  2. You are trying to solve the problem again. You ask why because you want more detail and you want more detail because you want to fix the problem. Slow it down.

It is better to reframe the questions starting with “why” to starting with “what.

E.g. "Why did you do that?" Can be reframed as "What were you hoping for there?" Or "What made you choose this course of action? What’s important for you here?"

4. The Foundation Question 🐠

Ask people what they want, because it will help you figure out the main problem. Think about this as a “Goldfish Question,” because it can cause people to react by staring at you and not saying anything.

Asking the question “What do you want?” – could be a very difficult question to answer. We often don’t know what we actually want. Even if that question is answered, “What do you really want” would typically stop them in their tracks.

Even if you know what you want and are courageous enough to ask for what you want, it is often hard to say it in a way that is clearly heard and understood.

"The single biggest problem with communication is the illusion that it has taken place." — GB Shaw.

A distinction should be drawn around wants and needs. Want = I’d like to have this. Need = I must have this.

In Marshall Rosenberg’s model of Nonviolent Communication, a communication process that “helps people to exchange the information necessary to resolve conflicts and differences peacefully,”  demonstrates the differences.

Wants are surface requests, the tactical outcomes we’d like from a situation. Needs go deeper and identifying them helps you pull back the curtain to understand the more human driver who might be behind the want.

Rosenberg explains that there are nine self-explanatory universal needs – Affection, Creation, Recreation, Freedom, Identity, Understanding, Participation, Protection and Subsistence.

When you ask someone “What do you want?” - listen to see the need that likely lies behind the person’s request. For example, when someone says:

  • “I want you to talk to the VP for me” - it is about protection.
  • “I want to leave early today” – it is about understanding
  • “I want to do a new version of the report” - maybe about freedom or identity.

However, when asking this question, employees' brains are scanning the environment around and asking itself, “Is it safe here? Or is it dangerous?”

That's why creating psychological safety is crucial.

The best way to create psychological safety in these coaching conversations is using Stainer's four primary drivers to consider with an acronym TERA:

  • T – Tribe – The brain is asking “Are you with me or are you against me”. If you are on its side, your TERA quotient goes up.
  • E – Expectation – This is about “Do I know the future or don’t I? If what is going to happen next is clear, the situation feels safe.
  • R – Rank - Are you more important or less important than I am? It is about how a formal title or on how power is being played out at the moment. If you’ve diminished my status, the situation feels less secure.
  • A – Autonomy – based on Dan Pink’s Drive. “Do I get a say or don’t I”. That is the question the brain is asking as it gauges the degree of autonomy you have in any situation.

Asking questions like “What do you want” Increasing the TERA quotient, the sense of tribe-iness, as, rather than dictating what someone should do, you’re helping them solve a challenge.

The Miracle Question

Therapists talk of a miracle question – “Suppose that tonight while you are sleeping a miracle happens. When you get up in the morning tomorrow, how will you know that things have suddenly got better?”

The miracle question helps people to courageously imagine what better really looks like.

The Foundation question “What do you want” is direct and has the same effect of pulling people to the outcome and once you see the destination, the journey becomes clearer.

5. The Lazy Question 💤

The question “How can I help?” forces your colleague to make a direct and clear request. Also it stops you from thinking that you know how best to help and leaping into action. Or being more blunt – you could ask: “What do you want from me?”

If you’re in a situation where you do want to engage in helping your team member solve a problem that they’ve been very protective of, and reluctant to ask for help, using “How” questions as demonstrated by Chris Voss in his writing of Never Split the Difference, is a great tool to demonstrate collaboration.

How questions invite collaboration.

A way to soften this question is to use phrases like, “Out of curiosity”, “just so I know”, “To help me understand better”, “To make sure I am clear”

When you’ve asked a question and they don't have an answer ready within the frist two seconds, instead of filling up the space with another question or the same question rephrased or a suggestion or just pointless words, you should take a break, stay open, and keep quiet for another five seconds.

Silence is often a measure of success. It may be that the person you are coaching is the type who needs a moment or two to formulate the answer in his head before speaking it.

This is about giving that space.

Stephen Karpman has come out with a Karpman Drama Triangle a variation take on the Transactional Analysis therapy model where he says we are dancing between three archetypal roles – the Victim, Persecutor and Rescuer – each of which are unhelpful and dysfunctional as the other.

These three labels are not descriptions of who you or your employees are. They are descriptions of how people are behaving in a given situation.

No one is inherently a Victim / Persecutor / Rescuer.

These are roles we end up playing when we have been triggered and in that state, find a less than effective version of ourselves playing out.

6. The Strategic Question ♟

“If you are saying Yes to this, what are you saying No to” is a strategic question asking people to be clear and committed to their Yes.

Too often we halfheartedly agree on something or more likely there is a clear misunderstanding in the room as to what has been agreed upon.

The Types of 'No' answers

The ‘no’ of omission – options that are automatically eliminated by your saying ‘yes’.

The ‘no’ of commission – uncovers what you now need to say to make ‘yes’ happen

It’s all too easy to shove another yes into the bag of our overcommitted lives, hoping that in a magical sort of way it will somehow all be accommodate.

This second type of 'no' puts the spotlight on how to create the space and focus, energy and resources that you’ll need to truldy do that Yes.

This is a great time to bring back the 3P Model of Projects, People, Patters to get clear on the nos.

Saying Yes more slowly allows you to shift  the focus and not over commit. It means being willing to stay curious before committing.

Projects People Patterns
- What projects do you need to abandon or postpone?
- What meetings will you no longer attend?
- What resources do you need to divert to the Yes?
- What expectations do you need to manage?
- What relationships will you let wither?
- What habits do you need to break?
- What old stories or dated ambitions do you need to update?
- What beliefs about yourself do you need to

Opportunities to say 'No'

Asking more questions to help you uncover opportunities to say no:

  • Why are you asking me?
  • Whom else have you asked?
  • When you say this is urgent, what do you mean?
  • If I couldn’t do all of this, but could do just a part, what part would you have me to do?
  • What do you want me to take off my plate so that I can do this?

The other Five Strategic Questions:

  1. What is our winning aspiration? Framing the choice as “winning” rules out mediocrity as an option. If you want to win, you need to know what game you’re playing and with (and against) whom.  
  2. Where will we play? “Boiling the ocean” is rarely successful. Choosing a sector, geography, product, channel, and customer allows you to focus your resources.
  3. How will we win? What’s the defendable difference that will open up the gap between you and the others?
  4. What capabilities must be in place? Not just what do you need to do, but how will it become and stay a strength?
  5. What management systems are required? It’s easy enough to measure stuff. It’s much harder to figure out what you want to measure that actually matters.

Let the employee choose what you will do and what you won’t do, that is the premise of the strategic question. “If you are saying Yes to this, what are you saying No to”

7. The Learning Question 📚

People don’t really learn when you tell them something. They don’t really learn when they do something.

They start learning, start creating neural pathways only when they have a chance to recall and reflect on what just happened.

Chris Argyris coined the term “double loop learning” – in the first loop, you are trying to fix a problem and the second loop is about creating a learning moment about the issue at hand. It is in the second loop where people pull back and find the insight.

A question that drives the double loop learning is “What was most useful for you”?

Adding “for you” to the question takes it from the abstract to the personal, from the objective to the subjective. Also it will give managers guidance on what to do more of next time and it will reassure  they are being useful even when they are not giving advice but are asking questions instead.

When we take time and effort to generate knowledge and find an answer rather than just reading it, our memory retention is increased.

If we, as coaches, ask you a question and you generate an answer yourself, the odds of your retention / doing it greatly increases. This is why advice is overrated.

Final Thoughts

In this blog, you learned the important of having a culture of development in your company, and why it's so crucial that your managers act as coaches.

At the same time, we included tips on how to host effective 1-1s and the five must-have coaching conversations.

The Seven Essential questions should now be part of your and of your managers' repertoire and everyday conversations, you will work less hard, you will have more impact and boost your career.

The real secret sauce is to build a habit of curiosity – finding your own questions, find your own voice and build your own coaching habit.

So to review, the seven questions are:

1. 🦵🏼 The Kickstarter Question is the way to start any conversation in a way that is both focused and open: “What’s on your mind?“
2. 😱 The AWE Question question works as a self-management tool for you and as a boot for other six questions:  “And what else?“
3. 🧐 The Focus Question: is about getting to the heart of the challenge – so you have got your attention on what really matters “What is the real challenge here for you?“
4. 🐠 The Foundation Question: is about defining the outcome “What do you want?“
Bonus: Miracle Question: Suppose a miracle happens tonight while you are sleeping. When you wake up, how will you know that things have suddenly gotten better?
5. 💤 The Lazy Question will save you hours:  “How can I help?“
6. The Strategic Question will save hours for those you are working with:  “If you are saying ‘yes’ to this, what are you saying ‘no’ to?“
7. 📚 The Learning Question: “What was most useful for you?“

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