Welcome to the third installment of my office hours articles, discussing real life leadership challenges. Leadership need not be a lonely or isolated pursuit. I’m a leadership coach and I’m here to support you and help your leadership shine bright.

Challenge #3 – Leading Yourself


I’ve been working for a few years in a startup production company. The owner is a relative and is a visionary individual.

He thinks he did me a favor by hiring a PhD, (myself), right after graduate school when he didn’t need one. My perspective is he couldn’t have succeeded without somebody like me; my project management skills; being able to under-pay a relative.

The visionary never recognizes the 101 things I get done under-budget every day, but points out every small omission. We are under-staffed and short on budget. There are always things that cannot be attended to.

While I focus on long term production activities, I get faulted for aesthetic blemishes. Explanation of my perspectives seldom make sense to the owner.

Being a relative, it is hard to quit and find a job. However, I am at that point.

J.D. (no their real name)


It sounds like JD has been battling in choppy waters for a while now. I see someone experiencing the pull of competing values and priorities, and a lot of dissonance. You’re having a tough time, and it’s coming to a head (“I am at that point”).

How does this experience impact on you?

I have a hunch JD feels they are doing the owner a favour.

I’m still surprised at the taboo around talking about emotions in the workplace. Sometimes the ‘self-management’ part of emotional intelligence is seen as suppressing or discounting emotions.

Talking is important. Sometimes we get stuck in that maelstrom of feeling, unable to find a way out, unable to find our own leader within. 

And sometimes we just have to ride the storm, to process it, before emerging with new energy and direction. (I’ve been there too – processing feelings of being cheated and upset at work; battling through fear and anger after an accident, to emerge with calm and focus.) 

Exploring, and naming what’s coming up for JD in the moment may be useful in getting unstuck. So I offer the question, how is this impacting you? Sometimes we need to clear the air before we’re ready to talk about what really needs to be talked about.

What’s important to you about this?

JD does a great job identifying personal values here, by virtue of feeling them being trampled. Values are critically important, and mostly live in the background of consciousness. Surfacing these values and naming them helps us see where we are. If we have strong values around respect, but feel we are never respected, that’s going to hurt.

Doing the work on value identification is also productive. It helps to clear the fog of bias – we can guess that JD might enter every conversation with the owner having already written both parts of the dialog. By focusing on values JD is working with what they know, what is true. JD can work with that and find evidence of how well, or not, these values are being honored in the current situation, and find some clarity.

What’s true in this situation?

There’s likely some assumptions being made here; interpretations of events. I want JD to be clear for themselves about what is true and what is assumed.

  • The owner “is doing JD a favour”
  • The owner is “visionary”
  • JD is being “under-paid”
  • JD’s perspective “never makes sense to the owner”
  • “Being a relative it’s hard to quit”
  • It’s hard “to find a new job

What’s at stake here?

We’ve spent a little time clearing the air, making space for JD to move forward. JD has identified important values and acknowledged the extent to which they are being honored. And JD has acknowledged what is true, and what might be untested assumption about the situation.

So from this calm eddy, what needs to happen?

What are we really talking about?

Family relationships; a difficult boss; workplace culture?

Is this challenge about working for a difficult owner/boss? JD certainly is not alone in this! The ascribed difficulty is generally the result of unresolved differences in working style, clashing of values/priorities, or competing or non-communicated purpose and vision.

So, if the challenge here is to improve the relationship then JD has options. But why should JD do the work? Because JD is invested in doing so and wants it to be better. The owner hasn’t asked for help, JD has. And changing the owner is beyond JD’s control, whereas JD can control how they change their interactions with the owner. We each co-create patterns of communication with others, so we are able to modify and change those patterns.

Is this about money? If JD were being paid enough such that money were not an issue, then how would the situation be? If money were the only difference, and values were still be trampled and the relationship with the owner unchanged, how would this be? How much does JD want to earn in support of the lifestyle they want?

Are we talking about the difficulty of finding a new/better paid job? Using their current learning, what would JD need to do to validate a new job is a better fit?

Is this challenge about quitting a job with deep familial relationships? What is JD assuming the impact might be, and how can those assumptions be validated? What are the consequences JD sees around this outcome? JD cannot control the reactions of others, but is responsible for their own actions and truth.

If JD is feeling stuck, and wants to find new angles to look at the situation, there’s plenty of room to do this. JD has to do the work here, but a good coach will guide a client in discovering their own new insights and options. This work can be a lot of fun and generate energy.

Or are we talking about something completely different? Perhaps the situation highlights unrealized impact. Perhaps we’re talking about life-purpose and identity. Our coaching would take a different path again in this instance.

Getting clear on the topic is important. Without this frame there can’t be real progress.

Tip: The Miracle Question

There are many ways of asking the same question, and finding what works for a given person is invaluable. The field of Solution Focused (brief) Coaching offers the Miracle Question. In essence the question is presented as a thought experiment/visualization, summarized below:

Suppose a miracle happened overnight while you were asleep and the problem went away. Tomorrow, when you go about your day, how would you know?


I invite you to pause here a short while and think about the signs you’d see.

What has observably changed?

  • You have email notifications for interviews of new jobs?
  • You have a pay rise?
  • You get praise from your boss?
  • You’re offered a redundancy package?
  • You hand in a letter of resignation?
  • What else?

All this underlines the importance of establishing the topic which oftentimes lies several layers beneath the froth of daily life. This is why I deliberately do not hold a perspective on JD’s situation. I’d be making assumptions, simplifying and filtering someone else’s experience, presuming what was right for them without checking. I’d be applying my own bias and values. 

What are you willing to do?

JD has described a difficult situation and there are potentially complicated relationships at play. My wish for JD is that they can identify actions to move forward that come from a place of choice, where the action is supported by their values, and is workable in all aspects of their life.

Coaching should never be about action for action’s sake. A client’s well-being is paramount, client’s are held as being creative, resourceful, and whole – they are the best expert in their own life.

Actions and consequences

JD could test the ‘ecology’ of potential actions. Here “ecology” is the NLP term referring to the study of consequences – “…a concern for the overall relationship between a being and its environment. The overall relationship between a person and their thoughts, strategies, behaviours, capabilities, values and beliefs.

Cartesian Questions

For each candidate action JD could ask the 4 Cartesian questions

  • What would happen if I did?
  • What would happen if I didn’t?
  • What wouldn’t happen if I did?
  • What wouldn’t happen if I didn’t?

Request for JD:

Will you brainstorm 10 different actions, choose 3 valuable ones and apply the cartesian questions to each of those 3, by the end of the week?

What would you offer JD to lighten the load of this leadership challenge? Please add to the comments. And also please share your feedback about this office hours leadership challenge.