Focus on leveraging each leader's strength rather than fixing their deficiencies. Studies have shown that when a leader's best talents and skills are engaged, developed and put to good use, the best results can happen. Trying to coach square pegs into round holes only leads to frustration for both the one being coached as well as the organization around them.
Do not just isolate one individual for coaching. Unless you are engaging someone yourself for your own leadership development, isolating one person on your team for coaching centers them out from the rest and makes them look like a problem that needs fixing. At a minimum, include yourself in the coaching if you feel you are having difficulty with a direct report. However, you will get the best results by involving more of your team in the process of self-development.
Make coaching voluntary and not mandatory. You do not want your team members to feel that coaching and development is being forced upon them, at least not initially. There is no point coaching someone who will fundamentally resist that coaching; it will not work. Let coaching engagements spread and ripple through your organization, like a stone does when thrown into a pond. As good results are achieved for the early innovators, latter adaptors will come around to see the benefit and will get on board, or risk being left behind.
Employ a multifaceted assessment approach. Appraising a leader's capabilities is important; however, it is not the only quality to assess in your leadership team. Assessing a team member's job roles and career direction will help guide you and them as to where their focus should be in order to bring out their best in the organization, both in the short and long-term. Also, examining their personal style and behavioral preferences can help them both design their work and adjust their people approach so that things flow more smoothly due to greater self and other-understanding.
Give your team a choice about whom they want to work with. Have your team members interview 2-3 potential coaches and align around one provider (or one firm of coaches) that they think will best support their success. However, be careful in choosing different coaches (or different firms) for different members of your team. You want everyone to align around a common set of coaching principles and practices rather than team members going off in different directions with different coaching approaches.
Model what you expect from your team. By starting with your own leadership development, you set an example for others to follow. You cannot expect others to take on a course of self-development if they do not see you doing the same for yourself. Step up to the plate yourself and be what you hope others will also become.
Leverage coaching for organizational and top-team development. Your coach will be in a good position to help you address larger organizational and business issues by coaching your top team members. Therefore, you want a person who is versed not only in executive coaching but also in organizational effectiveness.

Harvy Simkovits, CMC, President of Business Wisdom, works with owner managed companies to help them grow, prosper and continue on by offering innovative approaches to business development, company management, organization leadership and learning, and management education. He can be reached at 781-862-3983 or .