Leaders, take note!: 4 must-have coaching questions

By Devon Brown on April 11, 2017

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As leaders, coaching and developing talent is imperative. Leaders constantly balance day-to-day demands, crises and short-term priorities with longer-term strategic and big-picture thinking. With all of this weighing in the balance, it’s not surprising that coaching, mentoring and developing are consistently some of the lowest scoring competencies across many 360° assessments, including the tens of thousands of respondents to Linkage’s Leadership Assessment Instrument™.

What’s interesting about this data is that it’s consistent across many levels of leadership. We find that front-line supervisors are as likely to struggle with the necessary skills as well as finding time to coach as executives are, even though their focuses are significantly different.

Coaching Is Not One-Size-Fits-All
To coach effectively, you must know and understand the people that work with you—especially those reporting to you. Sounds easy enough, right? Not so much. In addition to the aforementioned time constraints, the needs of one direct report can be drastically different from those of another.

I recently had a call with a coaching client who is a COO at a hospital. One of his directors has been in the role for 42 years (which happens to be 12 years longer than my client has been alive), is completely happy, and does not want to move in to any other role. Another director is in his late 20s, and is being groomed for the COO role. Being able to identify and understand the coaching needs of each direct report is critical.

4 Must-Have Questions to Get Started
Coaching requires a skill set that not all leaders are familiar with or have practiced. The following questions provide a framework for these conversations, as well as offer a test for how well you know the development needs of your team. Always keep in mind that this is more about exploration and asking, and less about telling. In your role as a leader-coach, these questions are guides for discussions and conversations.

1. Facing the Future — What do you want to be when you grow up?

This type of question helps people explore where they want to go in their careers, their aspirations, short- and long-term goals, what’s important to them, etc. This dialogue helps set the stage for creating goals and can guide the directional focus of the coaching.

Other questions that can help you explore their future state are: What personally motivates you? What work engages and excites you? What is important to you in your life and at work? What do you want to do that you are currently not doing?

2. Leveling the Playing Field — What are your current strengths and weaknesses?

With this question, you’re exploring current strengths and weaknesses (or development needs). It’s also valuable to explore the strengths that might potentially derail them if taken too far or used in excess. For example: Do they have certain behaviors, habits or attitudes that may have helped them get to where they are but are now inhibiting them in their current (or future) role?

Other questions to ask might include: Where have you been most successful? Where have you found yourself struggling? What have you done in the last six months that you are most proud of, and how did you achieve these results? What have you done in the last six months that you are most frustrated or disappointed about, and what got in the way of the desired results?

3. Identify the Gaps — What are the gaps between where you are now and where you want to be?

Here, you’re having a dialogue that combines your knowledge of their current state with where they want to go. Focus on identifying and clarifying the key skills, experiences and mindset necessary to be successful in a future role, or to operate in a greater capacity or perform at a higher level, and then pair this insight with the reality of the current state. By focusing on the future and current state, you will be able to identify and clarify key critical areas of focus.

Other questions to help explore the development gaps are: What are the skills, attitudes and experiences necessary for this future role, position or performance? Where do your skills, attitude and experience match those expected for this role, and where are there gaps? What are the top two to three areas to focus on in your development?

4. The Plan of Attack — What is the action plan?

In the final step, you’re developing a plan for how your direct reports will gain the necessary skills, experience and mindset to grow, develop and progress in their current role, future roles, and in their career. In this step, look beyond training opportunities and focus on how they can be developed in their role while doing work that both adds value for the organization and provides new growth opportunities for them as an individual.

Other questions to explore are: What projects or stretch assignments are you interested in taking on? Is there work that you are not currently doing that you would like to do? Which stakeholders should you be building relationships with? What departments do you need to better understand and work more closely with?

Coaching for Your Present and Future States
If you don’t have answers for these four questions, then you have an opportunity to have conversations with members of your team. The true value is not just in the answers, but in the dialogue that results. Your direct reports will feel valued and heard, and empowered to take an active role in their development and growth—both now and in the future.

And for you, as a leader, this process provides valuable insight into both the current and future state of your team and equips you to take care of your most important assets—today, tomorrow and into the future.

Posted in Blog, Coaching, Leadership Development

About Devon Brown

Devon Brown is a Principal Consultant at Linkage. He has more than 20 years of experience in developing, designing, and facilitating leadership development programs; providing executive coaching; and consulting around strategy and organizational design. He has expertise developing leaders and working with teams and organizations to solve complex problems.
3 comments on “Leaders, take note!: 4 must-have coaching questions
  1. Todd says:

    Hi Devon,
    One thing I believe is critical is the environment in which this is conducted. If it is not fully communicated as a growth path, it can very well be scene as an exit strategy. “Let me tell you my weaknesses and where I need to improve”. Unless a totally honest, healthy environment, results will not be what you need. My personal experience is, if the leader has not built this trust, they should not attempt to coach, as motive, etc. will be questioned. I have been on both sides of this.

    Other than that, I like what you have outlined.

    • Devon Brown says:

      Thanks for your response Todd. I absolutely agree. Context and intention matter. For coaching to work and to be seen as a value-add, it needs to be distinguished from general feedback (which is in the moment and not necessarily tied to a bigger development process/goal) and from performance improvement and a PIP. For a leader to be a valuable “coach,” they must be in a culture that supports, values, and rewards learning, development, and growth, and above all, as you said, a relationship that is grounded in TRUST.

  2. KUMAR VS says:

    Simple. Powerful. Thanks

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