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Coaching FAQ

How do we get started? 

If we agree to work together after the initial meeting, we'll start with a 90 minute kick-off. During that session we'll go over the basics and logistics. I'll also get to know you better as a person and as a leader. In advance, I'll ask you for some background on you, your team, and your company. Then we'll work on identifying your development goals and make a plan to achieve those. 

How long does a coaching engagement last? 

I don't have a fixed duration. I organize engagements into 4-6 month cycles with goals in each cycle and evaluations at the end of each cycle. That creates natural break points. Some people I work with for a single cycle, others for years. I prefer long-term relationships. Also, sometimes the intensity waxes and wanes from biweekly to monthly and back, as needs change.

How do you measure results? 

We'll evaluate results together based on the goals you set. I encourage coachees to consider the impact on the business, their team's performance, and the coachee's visible behaviors and competencies, as well as how the coachee feels. At the beginning of a cycle, it's ideal to identify a group of people who will be in the know on the changes you're making. This group can be a quick source of feedback along the way and at the end of a cycle. They also become champions of your change. In addition, when it makes sense, we might do a lightweight survey of stakeholders. 

Can you tell me more about 360 reviews? 

I highly recommend 360 reviews. They're a powerful way to get candid feedback, which most CEOs never receive in the normal course of business. I do two types of 360 reviews: 

  • Lightweight - This includes 3 - 4, 30 minute, 1:1 conversations with different stakeholders: ideally, a board member or your manager, 1-2 reports, and 1-2 other people with some insight into your leadership. I give you verbal feedback on what I learned. 

  • Complete - For a complete 360, we identify 10-15 raters. I’ll run a survey called a Leadership Variability Index (LVI) and do qualitative interviews with most of the raters. I’ll compile a detailed report and recommendations. We’ll do an in-depth debrief on the feedback and a second in-depth session to create or calibrate your developmental goals and plan.

I only do 360s with regular coaching clients. If you do a complete a 360, I recommend a progress report (simple survey) after 6 months. 

Where are you based? 

I'm based in Boston, but I work with clients anywhere I mostly work virtually.

When do you do sessions? 

I normally do sessions between 10:30 AM ET and 4:30 PM ET, but I'm flexible. I can always be reached by text and email. Also, I can jump on a call anytime for urgent discussions. 

How many clients do you work with? 

Normally, I'm working with anywhere from 10 - 20 clients. 

Do you have a blog, podcast, book, webinar, etc?

No. There is already plenty of content about leadership and management. I curate and share the useful stuff, when it’s helpful. Finding good content about leadership is straightforward. Actually changing yourself so you do it consistently is surprisingly hard. 

Do you ever work with non CEOs? 

Yes. I primarily work with CEOs, but I also with executives and co-founders. 

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