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Confronting Your Toughest Coaching Challenges


While there may be some bumps on the coaching road, we’ve identified the five common challenges that arise when working with attorneys and other professionals in the process together with strategies for addressing them:

1. Challenging/skeptical about what can be achieved in the coaching process:

  • This is where the coach’s level of professional influence becomes critically important! When dealing with a skeptic, I talk about my years of coaching experience (credibility/authority), and the success similarly situated clients have achieved (social proof). This works best if you have a couple of successes with influential firm lawyers who are known to the skeptic. Share those stories - without betraying confidential info - and lay it on thick!

  • Ask the client is he/she has worked before with a voice, acting or sports coach, or even with a tutor – the concepts are similar. Did he/she succeed with that work? Why or why not?

  • In drastic cases you may suggest that perhaps the attorney is correct: he/she may not be able to achieve the coaching goals he/she seeks. And because you are engaged in coaching a number of other firm lawyers who are working hard at the process and succeeding well, you certainly will understand if he/she decides not to work with you. Challenging a challenger is often an influential strategy for advancing the relationship.

2. Blaming others for why the client cannot succeed:

  • Ask for clarification of how someone else’s conduct or belief has created limitations for the client. Don’t cut this client off too quickly because he/she typically has a laundry list of reasons that you need to understand for why he/she hasn’t been able to succeed.

  • Ask the client to “suspend his/her disbelief” and discuss what would happen if these limitations imposed by others were removed.

  • Are the limitations real in all respects? Is the client willing to explore this issue with you?

  • What one or two things could the client do to work around or compensate for the limitations?

  • In drastic cases – where clients truly believe that there is nothing to be done to remove or address the limitations imposed by others – sometimes I “call his/her bluff” so to speak, and suggest that perhaps coaching is not going to be helpful for in light of the insurmountable difficulties he/she is facing. Usually the client back pedals then and decides that perhaps there is something he/she could do to overcome the obstacles.

3. Going through the motions – wanting to get an “A”:

  • This person seems to be working through a list of activities, but when you listen well and take notes you realize that he/she is churning the same old checklist of non-strategic activities. In other words, he/she is not engaged in the process with you. Oftentimes this type of person seeks acknowledgement and simply wants to get an “A” for effort, but isn’t particularly interested in getting results.

  • It usually takes two or three coaching meetings with this client before you have enough experience with him/her to recognize the churning process. At that point it may be helpful to tell the client your notes indicate that he/she has been working the same list of activities for several months but doesn’t seem to be making much progress. In addition, those activities don’t track with the strategic coaching plan you created for him/her. Say/ask: “When we started this process we spent a lot of time identifying certain goals and action steps to reach them. Has something changed since then? If not, then why are you focused on those other activities?”

  • It may also be that this client is not really interested in change, but is going through the motions so he/she can tell a practice group leader or other higher up’s that he/she is working on business development. Give him/her a chance to prove you wrong by using the strategies listed above. If there is no change in approach or attitude, then have an honest discussion about whether coaching – or coaching with you – is the right process to pursue.

  • This may be the type of client who needs you to impose greater structure on his/her activities and assignments. Ask him/her to spend ten minutes before each coaching meeting jotting down what he/she would like to work on in the coaching meeting that day. At the end of the coaching session, summarize with him/her what you’ve discussed and the activities he/she has agreed to undertake prior to the next coaching session.

4. Fearful of Change

  • ​ Despite an intellectual commitment to getting better results, many of us are afraid of moving out of our zone of comfort in order to achieve success. This is especially true in a law firm culture where we look to precedent and what went before as a guide for our own success.

  • It’s important to always make a distinction with clients between substantive success in your law practice (i.e., where success is linked to respect for precedent, case law, regulations, etc.) and success at business development which depends on identifying competitive advantage and taking calculated risks to build new business. A similar contrast may be drawn for certain professional development behaviors the success of which depends on our willingness to take calculated risks in order to be more effective.

  • Often I ask coaching clients to “act as if,” in scary professional situations. “Act as if you are an outgoing person when you go to the firm retreat. Think about a particularly outgoing person you know, and identify a few of his/her behaviors that you wouldn’t feel too ridiculous mimicking. “ When I first started consulting 13 years ago, I often felt scared and anxious. So I’d conjure up the image of a successful person and say to myself: “What would she do in this situation?”

  • With coaching clients, I refer to fear as “stage fright.” Stage fright gives performers a certain competitive edge. It causes them to practice thoroughly, think through things that may go wrong, and otherwise prepare well for the challenges that lie ahead. There’s nothing wrong with stage fright. I fear the day when I no longer experience it!

  • If someone is truly paralyzed by fear of change and unable to take small steps to effect it or to practice new behaviors in low-risk situations, then he/she may need a different type of support than coaching. When I see a client who is chronically anxious and unable to make progress in coaching , I have an obligation to recommend that he/she seek guidance from a counseling professional.

5. Inability to form a positive bond with the client- i.e., as a coach I have resistance to the client

  • This is a rare challenge, in my experience. I can only think of two situations (among the 100 plus attorneys I have coached) where I couldn’t find anything positive about a client that I could connect with in order to support his/her coaching success. In those two situations I had an obligation to tell the clients that I felt I was not the right resource for their forward progress. In both cases I directed them to other coaches who I felt might be a better fit.

  • Self-awareness is key to coaching success. I need to be aware of judgments that I make about my coaching clients, their values and beliefs. While I am entitled to my beliefs and opinions, I may not allow them to interfere with the coaching process. There must be a boundary between what I think and believe as an individual, and my ability to serve my clients as a coach.

  • As part of the assessment meeting, I “zoom out” and observe myself interacting with the client. I ask myself, “What is it about this person that I can support and cultivate? What good can they do for the organization with my help?” Usually I identify at least three to five specific positives and I keep those in mind when I encounter ideas or beliefs in the client that I don’t personally appreciate.

  • “Mirroring” another’s behavior often builds a positive bond in a business setting. So if I’m with a particularly anxious person who talks constantly, then I need to allow him/her to vent and listen actively to his/her concerns. If I’m working with someone who is challenging by nature, I don’t take that behavior personally; I realize that this is how he/she is with everyone! By recognizing behavioral differences between me and my coaching clients I’m often able to mirror their style and form a more positive bond with them as a result.

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