Dana and Michelle, closest of friends and partners in a thriving public relations and advertising agency in New York City, are struggling with a fast-moving change in their relationship and business. Dana finally decided to try working with an executive coach –almost in desperation.

After several email exchanges and a couple of phone calls, Dana initiated the process by introducing herself and the situation.

Process Narrative

Dana   10:45 AM Jan 10

Hi, my name is Dana. Not sure just where to start with this. Maybe I’ll just pretend I’m talking to you on the phone, which is what I do about 28 hours a day anyway.

The reason that I have decided to try out your executive coaching service is that I have tried pretty much everything else that I can think of, without getting anywhere. Here is my problem:

About ten years ago, my best friend Michelle and I started our own business as partners in a public relations and ad agency. Just the two of us at first, but we grew steadily to our current headcount of 125. We are not getting rich at this — too much competition for that — but we make a pretty decent living. We seem to work 24-7 most times.

My role starting out was to hunt business — almost anything that would pay us was fair game. I am pretty good at sales so it wasn’t too long before we had to add staff and to focus our roles on what we did best. Michelle is the back-office person who handles almost everything after I or my team get a signed contract. She is so great at this. Real detail person who never lets anything slide or get out without being perfect.

As we grew, these complementary roles became blurred. I started producing some of the jobs while Michelle gradually developed a solid client base of her own. In the past couple of years, she has begun to act as the boss of everything rather than the partner I want and need. We now argue a lot over small stuff. She tries to tell me what to do and I resist just to make my point that she is not the boss.

Our relationship has deteriorated so much that we hardly talk anymore. I have considered breaking away on my own a dozen times but I am not confident enough to do it without a Michelle to work with.

What should I do?

About me: I am 42 years old, married, one child finally in college. Family life okay but strained always by my work. David, my husband, is supportive but also struggling in his job as a tax attorney in a very big law firm. (That’s another story for another time.) Most years, I make quite a bit more than he does, so we are pretty well off financially.

I graduated from Radcliffe with a B.A. in French literature. Since then I have taken a few business courses at local colleges just to help me cope with the complexities of running our business. It just gets harder every year.

My hobby is sleeping, whenever I get time to pursue it. Actually, it is reading, which I treasure. Mostly older fiction by the greats. I have started golfing but it takes too much time. Good to do with clients, so I will keep at it whenever I can manage.

What are my dreams or goals in life?

That is a hard question because I hardly every think about anything other than the daily challenges. My biggest achievements are getting through each day without any major crisis or catastrophe. Maybe I am just getting burned out, as almost everyone I know claims to be doing themselves. Maybe not me, though, because I really love what I do.

I guess that my most important goal is to get this problem with Michelle resolved. It so overshadows everything else that it has to go away before I can even begin to think about what next.

What have I tried to do about this so far?

What haven’t I tried! I tried to talk to Michelle about “our” problem but she just brushes me off with a “what problem” attitude. She doesn’t think that there is a problem. So it’s really just my problem. So “get over it”. Talking didn’t work. Getting over it didn’t work. “My” problem just keeps getting worse.

We even tried a consultant who danced around this problem but was actually very helpful in getting some messy aspects of the firm straightened out. I talked to him a couple of times about Michelle and me but he didn’t seem to see any real issue.

I also talked to Michelle’s ex — we are still quite good friends — who pretty much confirmed my feelings about Michelle’s control-freak tendencies. He told me that these were a big factor in their breakup a couple of years ago. He had no idea how to help me, since he said he could not even help himself.

Oh yes, and my therapist. Everybody in the city has one, even if they are disgustingly normal and hang-up free like me. We have discussed my Michelle problem a dozen times but it keeps coming back to being “my” problem. No help here.

How important is this to me?

It is probably the most important challenge (I always like calling problems “challenges” to keep a positive attitude even though it rarely works for me) I face today. Work is a piece of cake by comparison. It is affecting my work and my family life and my attitude about myself — like maybe it IS my problem.

Time frame for resolution?

Yesterday would be great but I am now to the point where any improvement near-term would help a lot.

Coach   5:20 PM Jan 10

Welcome, Dana! Your story is especially interesting to me because I have worked with quite a number of small business owners over the years. All of them seem to have gotten into some sort of tough problem (or problems) in their journey. I now feel that it is a vital part of being in business for yourself. You learn important things.

My first sense is that you are working from a solid foundation — you love what you do. That is something not too many people can say, unfortunately. So we have a good place to begin working. Whatever we come up with, it almost certainly has to preserve your work as it is, to the extent possible.

From what you have told me so far, I do not believe that you are the problem. Michelle is. You are the solution to your shared problem, since I have to believe that Michelle truly knows how you feel. And is ignoring the problem.

Michelle seems to be riding high at this point. She very much needed your sales ability at the start to match up with her production abilities but, as her own client base has grown, she really doesn’t need you as much. Or maybe not at all. Tough to accept but it may be a fact that we have to deal with.

You mentioned that her marriage broke up a couple of years ago. This seems to coincide with your problem getting much worse. These two events are likely to be connected, since Michelle may not have much else to occupy her.

You don’t sound like anyone who is burned out. You have a positive tone with some lightness in it. Another good stone for a new foundation.

Let’s make a quick list of the foundation pieces we have so far:

  • You love your work.
  • The problem is not you; you are the solution.
  • You are still mentally whole, not burned out.

There is probably a fourth piece we should bring in — your business as a vital part of your life. I doubt that you would consider going back to work for someone else, ever. Is this correct?

If so, then your firm has to be part of the solution. You might, for instance, decide to break up the firm and continue on your own. Michelle may be willing and able to buy you out to help fund your escape.

Think about your firm today as being composed of two somewhat separate businesses. What aspects of the overall business do you and Michelle still share? How many employees are mainly with you and how many work mainly for Michelle?

You mentioned being financially well off. Would you be able and willing to invest in a break-away firm? Think about how much you might be willing to invest.

As an exercise, you might try to recast the firm’s financials in terms of two separate firms perhaps with a shared service unit. If you need help doing this, it is probably wise to get your own accountant rather than using the firm’s accountant. You probably do not want to alert Michelle while you are in the process of deciding how to move ahead. Ask your accountant also to add a shared service group to each of these internal “firms” to see what a completely standalone firm of your size might look like.

Would it be viable from a profitability standpoint? If not, what would you need to do to make it acceptably profitable? Which costs might be cut? Could you drive up revenues quickly enough? Don’t do anything too elaborate at this stage — just enough to tell whether a break-up might be feasible for you.

Think also about breaking away from Michelle, probably with some degree of acrimony and loss of someone you described as once your best friend. Is this friendship still strong enough to be worth an attempt to preserve it?

If so, we need to add a one-firm solution as an option. You can see that the decision you must make is beginning to look like a how-do-we-fix-the-firm vs. how-do-I-break-away-and-succeed-on-my-own.

Does all of this make sense to you so far?

Dana   8:15 PM Jan 12

I have to say first that you really throw people into the deep end right away! I truly had not thought about anything quite like you have described. To be honest – it seems refreshing but a bit scary. But, after a day to reflect on what you described, I am ready to dig in and find out where this framework might lead. Feels like an adventure …

What next?

Coach   2:55 PM Jan 12

Sorry about the cold-water start but sometimes it helps to set up a strong straw-man situation to break away from things that you have found don’t work. So, let’s get into some actions that you might want to take to make this picture more concrete.

Get an outside accountant to help you recast last year’s financials as outlined above.

Think about the option of breaking away from Michelle, assuming that it is financially feasible. Who would you want to take with you? How would their jobs change? Who would you like to take but you know would stay with Michelle? What would it take to replace what they do? What obstacles do you see in making such a separation happen?

Don’t do any of this in great detail. What we need initially is just an outline with a few important elements.

Now go through a similar thought exercise on what you might do to resolve the problem while staying with the current firm structure. No doubt you have gone through this already but revisit the exercise and make some notes for me. What obstacles do you see as being the toughest to overcome? Are there any aspects of your current situation that might help you?

What we need to have is your summary of where each of these exercises came out. We don’t need detail at this point, just the highlights.

We will dig deeper as we get further along, but only where it is necessary and productive.

Dana   11:20 PM Jan 22

Sorry for the delay in getting back to you but a (routine) crisis at work came up that just wiped out my non-spare time while it got resolved. Or I hope resolved. Major client. Michelle actually very helpful in getting us through this one.

It is going to take a while to get through your list, even in “highlights”, so don’t worry if there is a period of silence at my end. I’ll no doubt send you a bunch of questions meanwhile so the silence won’t be too silent.

[Many short questions and exchanges during this period (omitted)].

Dana   4:45 PM Mar 10

Well, that was a pretty substantial amount of work you gave me but it was valuable. I hadn’t really thought much before about a break-away solution option. Here is where I came out on each of your to-do’s:

I got an accountant through David’s firm to help me with the financials. Top person and did a great job. He says that a break-away option is definitely feasible financially and may be a great move long-term. Short term might be a bit iffy and require a sizable personal investment. So that’s good to know. It is pretty scary for me, I must admit.

My break-away game plan: To be very brief, I came out with a plan outline that might actually work. I would need to add a lot more detail and get the accountant to adjust the financials but so far it looks doable. More on this below.

My stay-with-Michelle plan: To be even briefer, I simply cannot see any way to do this and stay sane. Maybe you can help me here because I agree that I need to go through both primary options. I thought about adding a third option — do nothing and try to hang in — but finally decided I have had it with living that option. So two primary options it is.

I did think a great deal about losing Michelle as both a partner and a long-time friend. To my surprise, I came out thinking that I would miss her more as a friend than as a business partner. I am scared to death of going out alone to start a new firm but I finally realized that I hardly rely on Michelle for anything important these days. But I still value her as a friend (may be just me thinking that we are still friends). She has been an important part of my life for so long. Like getting divorced, I guess. You live through it, so Michelle says, but it leaves a big empty space for a long time. This feeling alone is enough to motivate me to make one last effort to stay with Michelle.

So there it is. The break-away plan is pretty clear to me in terms of people to take with me and holes that I have to fill. I will not count on getting any buy-out funding from Michelle. She will be much too angry for anything helpful, I’m sure.

And my stay-with-Michelle plan is empty. It cannot be a do-nothing type of plan, whatever we come up with. Do-nothing is not an option for me.

Where do we go from here?

Coach   4:26 PM Mar 11

Hi Dana — great job! I am now very comfortable with you as the head of a new firm if that is where you end up. Your response to my suggestions was excellent in every respect. Now on to the harder parts.

We have two options to work through. We have a very solid foundation to build upon. Both options are financially feasible at our current state of understanding.

Let’s first address your friendship with Michelle. Perhaps there is a way to help make this transition easier for her and so retain her friendship. We need to think this through as part of looking at our two options in more detail. I suggest we add “maintaining Michelle as a good friend” to your starting list of goals.

I am not at all surprised by your “empty” plan for staying with Michelle. If you had any good ideas for this, I am sure that you would have tried them by now. My conclusion is that everything you have tried has not worked but I may not know the whole story. If there is more that I should know about this, please fill me in.

To be able to offer suggestions on the stay-with-Michelle option, I need to know more about your interactions and friction points. What is working well between you and what is not? Were there any relationship-changing events that you can recall? What would Michelle have to change to make your relationship work acceptably for you? Going back to the good old days probably won’t be possible so could you think about what, today, is not working between you?

For the break-away option, we can move ahead more purposefully. Try sketching out an org chart for your new firm with names and roles for those people you are likely to be able to take with you. Beside each name and role, add a guess as to the likelihood that they would agree to move out with you — 10%, 50%, 100%. Then make a brief note about any problems you see in moving each person to a new firm — things like commuting, child-care, spouse/partner concerns. These may have to be listed on a separate sheet if there are many items.

Think about salary issues and benefits that might arise. This exercise need not be too detailed or complete — just enough to identify any situations that might be serious.

Then, think about the break-away process itself. Make a starting list of what you would have to do beginning with telling Michelle about your plans. This should be a starting list with just enough detail to see the main steps you foresee.

To summarize:

  • Anything more that I should know about your friendship with Michelle.
  • Your interactions and friction points with Michelle as just outlined.
  • A break-away option org chart with names, roles, likelihood of coming with you, and any individual situations or problems that you foresee. Do not send the chart to me yet but just provide me with brief descriptions of some of the more important issues and obstacles you discover if any.

I am looking forward to seeing what you come up with.

[Many short questions and exchanges during this period (omitted)].

Dana   11:55 AM Apr 25

Here is what I have managed to do despite some very hectic days and continuing problems dealing with Michelle. I am beginning to feel that my options are steadily becoming a single option of breaking away on my own.

More about Michelle and me:

We were college best friends. She comes from a wealthy family of doctors, lawyers, business tycoons and other high achievers. Not really very pleasant people but certainly successful in business. Their lives are a real mess, however. After Radcliffe, we went our separate ways for a year or so and then ended up working for the same Madison Avenue mega-agency. Our college friendship resumed and deepened over the years we toiled in the monster. We finally decided to escape and start our own firm. Michelle’s trust fund made this a fairly painless step, as did my surprising (to me, anyway) list of contacts that quickly turned into clients. We made money every year since.

Everything was fine between us until a few years ago — maybe 3 or 4. I was the salesperson and she ran the firm and got the work done. Michelle is really not good with people but absolutely great at getting things done right and on time. We have a high staff turnover because of this but it doesn’t seem to bother Michelle. This situation will probably make my moving out a lot easier for me since I am a buffer between many of them and Michelle.

Now I guess that I am moving on to your second question. Our interactions, good and bad:

Up to about 3-4 years ago, we interacted as friends more than businesspeople. We each did whatever needed getting done, without worrying about turf. I consulted with Michelle on anything that I felt she needed to be part of, and she did the same with me. We made a really great team. Then things started to change.

There was no event that I can recall that triggered the change. It just happened, mostly without us being aware that it was taking place. I think that it was about two years ago that I really caught onto the change that had taken place. Michelle was going through a sort-of messy divorce (all of her family has a messy divorce or six in their past) and she was increasingly distracted from me and the firm. I picked up the slack without thinking about it — it was what any good friend would do. That workload nearly messed up my marriage, which has had its rough spots apart from work pressures.

Michelle came out of the divorce changed. A lot. She was more intense and serious. And formal. We lost quite a few good staff people that year. I tried my best to make allowances for Michelle, figuring that she would eventually move beyond the divorce. Her family has so much experience doing this.

Anyhow, as the months passed, things not only didn’t get better but got steadily worse. Our interactions became brief and often involved arguments over small issues.

During this time, a number of our larger clients began dealing directly and almost completely with Michelle. She has a lot of family connections to help her but anyway she has pretty much set herself up as a firm within our firm. I have had to scramble to get new clients and keep the staff that works with me busy. Our high turnover had one benefit in that new folks with the right skills could be moved into our evolving situation.

I can’t think of any particular interactions that are more difficult than others with Michelle. Pretty much every interaction these days is difficult. Sadly, I can’t even think of one good interaction that we have now. We pretty much do our own thing and avoid each other as much as possible.

My break-away option org chart:

This was a pretty simple task. Only about a few dozen people involved — pretty much splitting the firm in half. My biggest problem may be keeping it to this size. All 52 people in my chart I think are 100% likely to move with me. I may have to deal with the problem of maybe 10-15 more wanting to come, which would effectively kill Michelle’s part of the firm. Can’t let this happen.

I see only a few minor issues with salary and benefits. We have such a high turnover that we have to keep pretty competitive just to attract new people. Current levels of both are included in my rough financials.

This exercise turned out to be quick and simple but worthwhile doing I think because it gives me some confidence that this dream might actually be possible.

You asked earlier about my dreams. Now I think maybe I have one.

What next?

Coach   11:55 AM May 1

Hi Dana — Again, truly excellent work. If you do decide to break away, you will be a fine firm leader. This is meant as a confidence-builder, not advice. I am convinced that you will come out a winner whatever you decide to do.

Thanks for the additional background on your relationship with Michelle. It is sad but things change. The divorce probably triggered the work changes you see but the latent problems were there long before. I gather from your comments about Michelle’s family that there is a history of high achievement and unhappy relationships. Michelle seems to be a solid part of this family tradition. She may be striving to lead your firm because that is what her family does well. Rejoining her family as a reaction to her divorce loss.

I am not a therapist so my theories are probably best left at this sketchy point. But you can take them where you think that they need to go.

Since we last connected, I have thought quite a bit about your option of trying to stay with Michelle. I have come away feeling that this option is unlikely to succeed but I want to get your feelings about this. Your gut feelings seem vital now.

I am happy to learn that your org chart exercise did not uncover any show-stoppers. You don’t really need an org chart for a firm of this size but it helps you focus on people issues that might be important.

Let’s make the next session a stay-with-Michelle effort. If you agree, here is what I suggest:

Think about breaking up but within your existing firm — essentially building two largely independent firms within your existing firm. You might even move to new offices — close by but separate. I have seen many successful professional services firms built on this principle. Share only those functions where you have no disagreements. Tell me whether you think that this is possible and if so, whether it might actually work.

If the cost is not unreasonable, recast your break-up financials into this firms-within-a-firm structure. It will probably work better financially — no investment needed on your part and no break-up costs. Identify anything that you see as a problem financially with this picture.

Lastly, think about how you might operate your internal firm within this environment. What issues do you think might remain? Are there any residual people problems that you foresee? How might this structure be better or worse than the break-away option in your view?

If you agree, I will look forward to your next session input.

Dana   10:30 PM Jun 7

Sorry for the long delay in getting back to you. Michelle and I have had a major fallout and have tentatively agreed to break up the firm. It was pretty nasty and I am barely over the traumatic final meeting. I think that we will be meeting with lawyers from here on. Sounds like a divorce, doesn’t it? Well, I guess it is.

I did a lot of work on your firms-within-a-firm concept before all of this happened. This approach was beginning to look pretty good until D-Day.

What triggered the break-up? A leak to Michelle that I was thinking of going out on my own. Maybe someone saw my printed process notes or saw what I was doing on the computer. No real idea how the word got out but it did and the reaction was fast and major. Michelle went ballistic in the worst sense of the term. Accused me of everything but starting the Iraq war. Terrible personal attacks. I could hardly respond in any sane way so I just walked away. The whole staff I fear heard much of her tirade. Bad stuff.

Any advice?

Coach   9:05 AM Jun 8

Hi Dana — I feel so sorry for you. Just as we were beginning to get somewhere on both of your options. But Mother Nature has a way of pushing things along in her own directions.

So you are now dealing with a break-up option alone. Or are you? Is Michelle a person who explodes on bad news and then forgets the blowup and goes back to business? Are you someone who can forget and forgive the blow-up?

I think at this point that you have to make a firm choice on direction. Michelle may well have done you a favor in her reaction. The long and deep bond between you may at last be broken. Yes?

Your message points to a break-up as the only way forward. But another may have surfaced as a result of Michelle’s behavior: she may be willing to entertain a buyout where you would own the firm as it is. She certainly doesn’t need the income as you have indicated. Maybe she would be willing to leave under some sort of deal.

Do you think that Michelle may have reached an end-point and may be willing to entertain a buyout offer? Just what this offer might be is another issue but let’s assume for the moment that it is “okay” in critical aspects.

Let me know your thoughts as soon as possible so we can work on the next step.

Dana   11:55 AM Jun 8

Thanks for the quick response to my message of angst. All of this really hurts so much.

Getting past my self-pity, I have thought about your questions:

Michelle is not a forgiving person. She holds slights and grudges forever and then some. Might she let this situation pass? I think not. I am sure not.

I am getting over Michelle, sad and happy to report. A couple of my staff who overheard our meeting (probably heard over most of the city as well) approached with deep concern and asked if I was leaving and if so, would I take them with me. They were scared of Michelle. I felt so bad for them.

Might Michelle accept a buyout offer? Maybe but only if it was so high that it would be impossible for me. She has to maintain face in her family of hard cases. Winning big is all that matters to them. So I can realistically forget about this “option”. Trust me here: it will not happen. Ever.

So I guess that we are left with the break-away option. Almost every one of the staff has asked me if I would take them along so, now I don’t know what to do.


Coach   7:33 PM Jun 8

Hi Dana — Some further thoughts.

Sounds as if much of your decision flexibility is being overtaken by events. This happens a lot. You have probably heard the saying that “life is what happens while you are busy making other plans.”

Based on your assessment of Michelle, it seems as if your only solid path now is to break out on your own. Let’s assume for the moment that this is the case and that you now have to decide whether you want to pursue the break-away option fairly quickly or perhaps try to come up with some additional options.

My sense right now is that your break-up with Michelle is already done in spirit and, to an extent, in fact. This is what is happening. You will have to move quickly to avoid having events drive the whole transition. Time to take charge if this is what you want.

Think about this and get back to me as soon as you can. Once you have told me how you feel about the next step, we can start work on that path.

[No word from Dana after this response for several months. My practice is to leave situations like this alone until the client initiates a contact. Sometimes people like Dana just need time to get comfortable with taking a major step in their life.]

Dana   8:00 AM Oct 30

I am terribly sorry for the long silence. You were right about where things stood. It took me a couple of weeks to accept this as fact. I had decided to get moving and had planned to contact you within a day or two, when, without any warning, my husband David left his law firm job and offered to work with me while I started up my new firm. He said that he needed something new to do while he figured out what to do next with his life.

Having David working with me, my need for a Michelle replacement vanished. He was a godsend and within a month we were up and running in new offices closer to my main client base. We started up with the several dozen staff members I listed on my draft org chart. Within weeks, six more of Michelle’s people left her and joined us here.

David finally figured out what he wanted to do — go back to school and get teaching credentials — so he could become a teacher in a college. He left the firm last week after nearly four months of great help and encouragement. I will miss him a lot but we are so busy right now that I hardly have time for anything. He starts grad school at Columbia in a couple of months so will still be available to help out for short periods if I get in a jam.

Best of all, I have finally found my Michelle replacement. His name is Roger. Unlike Michelle, he is a delight to work with and he is even better than Michelle at getting things done. The staff loves him. I am back to doing mostly sales, which is what I seem to do best. I may even try to take up golf again.

And Michelle? We have not spoken since our nasty break-up. Lawyers (and David) handled the firm split and the hundreds of loose ends that came afterward. I stayed out of it, mostly because I had all I could handle just getting up and running again. I have just learned that Michelle has bought a much larger firm, so that her staff now is probably 250 or so. No doubt she has settled into making their life a living hell. Sorry for the nasty remark — I truly hope she does well. And she will. Tough, smart, driven.

So, that’s where the world has taken me. Looking back at my process notes (these are so helpful), I can see that the main thing coaching did for me was to help me understand my situation clearly enough to act. Until then, I had been avoiding a lot of realities that were beginning to drive things. Sometimes you just need an outside voice (or notes in this case) to help you move beyond a problem and toward a solution.

I have no doubt that I’ll manage to get myself in another jam before too long and will need your help again. Thanks so much for all you have done for us. Dana.

Coach   6:22 AM Nov 3

Closing notes to myself:

Dana pretty much summed things up in her last note. This is typical of coaching — you start trying to help in one direction and end up helping out in something quite different. I am fairly sure that Dana would have moved ahead on her own even without coaching. But perhaps our rather brief, choppy process gave her a crucial push and the perspective she needed to take over and run with it.

Unlike therapy that can take years of weekly sessions, coaching of this kind can produce results in a very short time. I think that is because the issues it deals with are what I call “head and heart” issues, not anything business-dysfunctional. People seem to come to coaching with the intention of improvement and with lots of motivation. In this respect, they start well along toward achieving what they want.

Dana   9:50 PM Jun 26

I seem to be getting pretty good at getting into trouble. Hope you are okay with helping me out again so soon. Another one right out of the until-now clear blue sky: Michelle is back!

Seems that her acquisition was a mistake and she is now in big trouble of some kind. She just called me to ask if I might forgive her and maybe help her out.

I simply don’t know how to respond. Asked David and he just shook his head. Way down deep somewhere, I still think of Michelle as a friend despite our nasty breakup last year. My head says forget her but heart, or whatever remains of it, says think about it.

I thought about it for a whole two hours and then went for a long walk. Result is that both my head and feet hurt mightily.


Coach   7:00 AM Jun 27

Hello again Dana. Good to hear from you but very surprised that it is so soon. Looks like Mother Nature is back to her old tricks in your realm.

Suggestion: Call Michelle in your best business-person voice and ask what is going on in her world. Courteous but not overtly friendly.

Dana   11:50 AM Jun 27

OK, did it, pretty much as you suggested. Michelle saw right through my business-persona but actually moved on quickly to outlining her major, major mess. It seems like a real doozy, speaking technically as you say. She really does need help.

Would you be okay if I add her to our happy coaching family? I want to help her any way that I can but I’m desperately scared of doing this alone.