Answer this question well, your team will have role clarity, and a team with role clarity is one sign of good leadership.

Yes, and …

Among the folks I have worked with, those who seemed to perform well, had the most fun, and inspired others more reliably, were those who always went “outside” of their role.
Indra Nooyi, former chairperson and chief executive officer of PepsiCo, touched on role clarity when she wrote about how she got promoted in the corporate world:

Be really good at your job, then look at your role from a broader, higher viewpoint. Figure out how else you can contribute around you, and make your job bigger. That’s how you will be promoted because your job is already bigger.

Clearly, there is strong evidence that some ambiguity in our roles is constructive. Therefore as a boss, are there ways we can drag our teams into the abyss between “what am I supposed to do” and “what am I allowed to do” and make something good from it? I think so.

Instead of putting pressure onto yourself and your staff that roles have to be defined and rigid, aim it co-evolving the roles with your team. Consider role definition as one continuous exploration, one continuous mistake. Embrace a bit of role ambiguity.

How? Try these 3 steps:

1. Agree upon the role and responsibilities per the job description, establish strong foundations first.
2. Ask your team member to write down one thing he/she finds intriguing and fun to do, outside of what’s agreed upon in step 1.
3. No matter what your team members come up with, fully and truly support it, with actions.

I know. This sounds risky. What if my staff comes up with something completely irrelevant? What if my staff fxxks with me? (Well, frankly, if your staff chooses to behave like this, you need to work on other things first.)

Your staff will likely be confused and scared to come up with anything meaningful. They will likely be guessing what you “actually” want. They will be stressed out about coming up the wrong or dumb or “not-bold-enough” idea. They might think this is yet another convoluted scheme of yours to fire them.

That’s why it’s actually you, the boss, who needs to be the courageous and disciplined one and follow through with the promise that you will support them NO MATTER WHAT THEY COME UP WITH, for better, for worse, till death do you part. I came to believe in this approach because I had a boss who dragged me into this kind of ambiguity and hand-held me to grow my own role.

This was back in 2006, when I became the sales manager of footwear at Nike in Hong Kong. We were struggling with the sales of basketball shoes. We investigated our sales channel, reviewed our segmentation, devised new incentive programs, and did everything we could within the sales function to try to boost sales. But I wanted to look at sponsorships in high school basketball teams and see if there were things we could do there.

Team sponsorship was the function of the sports marketing team and at that time they didn’t have the resources to look into high school sports teams. It would take quite a bit of manpower to conduct the study. I asked my boss if my team could study the market. He said yes, but also gave me 3 goals:

This side project could not distract my team from our core role – selling. We were expected to continue to exceed our targets.

This side project could only impact morale positively. He expected my team to be more motivated after this stretch project.

The output of this project needed to be useful and the sports marketing director would be the adjudicator of that.

Next, he coached me to achieve these goals. He focused me when I was distracted, nudged me to pay attention to my team, sounded off ideas with me, and motivated me when shxt got hard. He truly let me do what I wanted to explore, and truly supported me with real actions. We had a lot of fun, learned a lot about the high school basketball scene, brought in additional sales from “teamsales,” and paved the way to my next role – Sales Director for basketball in Nike China.

What do you think? Does this sound too ambiguous? Or have you had experiences where you were supported to go beyond your role?

(Of course if you really think the problem is the person, bookmark this newsletter, and read about my thoughts on “Managing Others” instead)

The Problem of the Problem:

Often we didn’t get to thoroughly investigate a problem because we spent time arguing how we felt, justifying our intentions, what we did, what didn’t do, etc. We also often jumped into discussing options prematurely (and then wasting even more time debating why it’s premature to discuss solutions).

Try This Framework:

When investigating the problem, ask both sides to ONLY describe the “the context,” “what happened,” and “the impact” the way we saw them.

In other words, the things we ought to suspend are emotions, the why, judgements, and solutions. This method allows both side to compare notes and look at how each side understand the situation. It allows both side to focus on what happened.

A Sample Script:

Difficult to put into practice? You may want to structure the conversation into slightly more rigid steps to help both sides stay on track. Here is a sample script:

“Let’s investigate the problem and focus on the problem first. I promise we will get to the people, me, you, our teams, other humankind. I have found this approach less scary and more useful. Here is what we will do. We will take turns and share these 3 things:

1, Let’s describe the context and the circumstances as we remember them
2, Let’s share what we saw happened
3, Let’s share the impact we each witnessed”

Why Does This Work?

This is a structure that gives everyone in the conversation a chance to NOT get distracted. Imagine “the context,” “what happened,” and “the impact” as guardrails. These guardrails set the boundary of the path of the conversation.

Another way to think of these guardrails is to consider them as our protection. Just like guardrails on a flimsy bridge, focusing on “the context,” “what happened,” and “the impact” save us from falling into the abyss of feelings and judgements.

Pro Tip:

If you are discussing the problem with folks you don’t have a great rapport with, or if you sense that the participants are becoming fearful / avoidant / defensive, have all sides answer these 3 questions in private and then share them to everyone. This approach reduces the tendency of one side reacting and adjusting their answers base on the sharing of the other side.

I know this sounds mechanical. Furthermore, obviously, there are heaps of additional skills to deploy when navigating these kinds of conversations. But trust me, by just experimenting with this framework, the discussions will become more peaceful, productive, and, yep, empathetic.

Try this and share with me your experience.

All these experiences taught me a lot about being an employee and convinced me that “meet expectations” was the worst place to be.

You see, in the real world, these two categories of employees mostly don’t exist:

• Great colleagues who work hard and deliver great work
• Shitty colleagues who are lazy and deliver shitty work

I wish things are so black and white. In reality, most employees fall inside the “meet expectation”/”middle of the pack” pile. Most of us are not the best, not the worst, mostly okay, and never perfect. As a result, one of the most numbing management tasks is to decide whom to promote or fire from this massive blob of sameness.

When I had to lay off people, I had to pick from folks that never had a poor rating. The decisions were haphazard and fraught with personal relationships. I was crippled by a deep sense of wrong and suffocating guilt.

As for an employee, being in “middle of the pack/meet expectation” is a crappy position to be in. When I was fired, I never had a poor rating. Yet because I was just another one of the many, my performance and career prospects were decided by methods that were no better than a draw from a hat. I was crippled by a deep sense of injustice and suffocating shame.

I want to propose a few categories to break up the messy middle. These categories are less quantitative but more descriptive and nuanced:

1. Who are your colleagues who are great to work with, energetic, positive, but only do ok/adequate work? These are the employees who always put their hands up in town halls, who you want to hang out with at the bar during offsites, but aren’t your super stars when in comes to results.
2. Who are your colleagues who are role models of hard work but show uneven judgement and need a lot of hand holding? They work really really hard, but don’t want to / know how to evolve, and their stubbornness often lead to unsatisfactory decisions.
3. Who are your colleagues who are exceptionally gifted and high performing but are complainers/pessimists? Folks that your customers love, your employees relate to, and folks you wish you know how to quit them.

From experience, in order to make better people decisions, you can line these employee categories up against the goals, the values, and the culture you are nurturing in your teams.

Do you desperately need results because you need to raise another round of funds?
Are you at a stage where you must deliver a great product?
Or is your team at a size where clear and consistent culture and values is needed to pull everyone together?

They are “in the front, with the team,” and truly understand the business.

But what is the main purpose of spending time in the front? Is it about learning how to do the jobs of the frontline folks? Is it about knowing the intricacies of the operations?

Yes, and.

As a leader, when we spend time in the front, we have the opportunity to hone a few unique leadership skills:

1. UNDERSTANDING and ASSESSING the performance of the processes and people through observation, inquisition, and participation (in addition to reports and updates)
2. VALIDATING their understanding of key messages
3. REINFORCING the consistency of their understanding of key messages
4. CONVINCING the team that you are here to help them enjoy their job more and you CAN help them enjoy their job more.

So next time when you get onto the sales floor, or show up at the setup of a roadshow, challenge yourself to …

• Become more effective and accurate in understanding what they are doing and assessing how they are doing (performance)
• Be able to hear clearly what they are hearing
• Bring consistency to what they are hearing
• Have the answer to the question “What is the 1 thing I can do, ONLY I can do, for them?”

Because I have joined an on-demand coaching platform.

And this is the #1 suffering I have witnessed – “My boss does not appreciate me.”

I have had many conversations where my clients were in tears. 

They felt humiliated, ignored, unappreciated, unwanted. 

They questioned their self-worth.

They felt injustice AND helpless. 

These feelings spilled over into their lives outside of their offices …

Because a manager made a careless comment, or neglected a budding rift amongst the team, or weaselled out of a difficult conversation …

Bosses, we are bosses, and we have bosses. That means we already know what it feels like to have a good boss, that we actually know how to be a good boss. We just need to work harder to not be a bad boss. 

Base on all the coaching conversations I have had, here are 3 things “good bosses” can do, so then you don’t slip into becoming a “bad boss” and wreck souls:

1. Shut up for a tad longer, when you feel the urge to speak.

2. Involve a tad more, when you feel the urge to leave it to the team.

3. Stay in a conflict a tad longer, when you feel the urge to run away.

Go. Just try to be less of a bad boss. You will be surprised how much contentment you will be able to bring to others. Trust me.

“Accomplishments?” “Successful repetition of any endeavors?”

To me, Confidence is comfort:

• Comfort in knowing that we are playing a game of progress and not a game of perfection.

• Comfort that comes from the accumulation of experiences where I survive my own failures.

• Comfort in our own skin.

I try to apply this to how I want my team to feel.

• I want them to know that we are playing a game of progress.

• I want to create an environment where they can be in their own skins.

• I want them to accumulate experiences where we survive our failures.

Interpersonal savvy is “having a range of interpersonal skills and approaches. It is knowing when to use what with whom- customers, senior leaders, peers, external stakeholders, direct reports.”*

And the most important part of interpersonal savvy that we must master?

How savvy are we relating to ourselves.

Yet so many of us remain satisfied with mere learning and fail to add practice and training.

Why? Well, it feels good to finish a book or a TED talk. “I’ve learned something new” feels instantaneously rewarding.

Whereas practices and training guarantee stagnation, failure, frustration, and pain.

Therefore if you are trying to get your team to learn something, consider bringing these 3 elements to your team learning environment:

1. Inspiration
   TED talks are great at this. They inspire. Turn your lecture notes into TED talks. I know it’s easier said than done, but you should at least try.
2. Participation
   Design the training so then it includes individual and team activities. Another example of how to increase participation: Make 20% of your training lecture-based and 80% of it activity-based.
3. Celebration
   Invest the most time figuring out what to celebrate and how to celebrate.

Do you want to celebrate effort, or outcome, or both?
Do you know how your team members like to be celebrated?
Did you know that some people love the pedestal while others prefer a subtle pat on the shoulder?
Did you know you can ruin everything by forcing an introvert to make an Oscar winning speech in front of the team?

That you couldn’t land on a decision without disappointing someone?

That you wondered if you were too “democratic?” Here is an approach to lead through this.

Often when we discuss strategies and actions, we tend to focus on what’s possible: 

• What are ways we can execute the plan?
• What are ideas to go after our quarterly goal?
• Let’s brainstorm on all the different execution plans!

When there are many options or ideas on the table, things get tricky because of the interpersonal dynamics: 

• Teammates are invested in their options and ideas
• All the peer-to-peer and peer-to-boss dynamics come into play
• Most critically, you the boss are now forced to have to juggle between the perception of being “democratic” and “autocratic” 

One way to steer the discussion towards a more actionable direction is to move away from the POSSIBILITIES and move towards the PROBABILITIES:

• What is the likelihood of “Plan A” achieving our goals? 
• What are the probabilities of this option failing? Base on what supporting facts? 
• What additional information do we need to verify this probability?

Lastly, a thought to continue the thinking: 

How do possibility and probability relate to being in the present?

He felt overwhelmed and often second guessed himself. I relate to him. I felt the same too when I had to lead functions and professionals that were out of my wheel house. His self-doubts turned every action and decision he had to make into a painful drag. It got pretty bad that he began asking himself – “Is this who I truly am? I miss being a chef!” I shared the same thought often – “Is this who I truly am? I shouldn’t be wasting time dealing with office bureaucracies. I miss being a high functioning star sales!”

What I worked on with him was to help him feel less suffocated and stalled. We worked on getting him mentally “unstuck” and “forward moving.” This was how we honed his “mental mobility:”

1. Becoming aware of what is happening and how we are feeling

We worked on becoming more consistent in asking ourselves questions such as “What’s happening?” “What am I feeling about the situation?” What don’t I understand?”

It is very important that you are aware of how you are feeling. More often than not we let our emotions linger to affect our actions and decisions. The best way to remain calm and rational is to first notice how we feel.

Think about it. What would you do if you know you are feeling furious? We know it isn’t the best time to decide on anything when we are furious. Therefore the first step is to learn to become aware of how we feel. The first step is to try to create a bit of a gap between how we feel and how we react.

2. Expose the choices we actually have

We worked on seeing all situations through a buffet of available choices by asking ourselves: “What are all the available options?” “How do these fit into our current priorities?” “Why do I want to do this? Who and what am I doing this for?”

More often than not, we tend to be too subjective when we consider our options. We tend to be influenced too heavily by our emotions. For example, if we are feeling inadequate, we tend to only think of options that protect us from risks instead of options that explore possibilities. Or when we are feeling overjoyed we tend to only think of possibilities and do not consider the risks.

In summary, the goal here is to consciously become more objective in exposing and assess our options. The goal here is to help ourselves come up with options that are more balanced.

3. Strengthen self-trust

Lastly, I point to my clients evidence of why they should trust themselves. More often than not, I trust my clients more than they trust themselves, because as a non-judgemental observer looking from the outside, I have a much clearer view of how my clients lead and act. Ultimately, through the coaching relationship, I want my clients to see themselves objectively and operate from that vantage point. I want to remind my clients that they are mobile—that they have the capability of choice and can move in the direction of their desired ends.

This is something that will take time. It is very important that we have a balanced memory of ourselves. Only when we can assess ourselves objectively, we can trust ourselves more. The best way to approach this is to keep track of our successes and failures. We have to work on building the evidence of our successes and failure.

From my experience, having an up-to-date list of our successes and failure gives us the best chance to be as objective as we should when we have to evaluate ourselves. Having an up-to-date list allows us to rationally decide whether or not we should trust ourselves.

Try it on yourself or with your team.

1. Try to become more aware of feelings and self talks.
2. Objectively brainstorm and assess options.
3. Force everyone to look at both evidence of success and failure equally.

Let me know how it goes.