About 10% of my active client pool is in transition, looking for new jobs or even new careers. The real coaching work begins after they land their new job, often choosing between competing offers, especially these days in the Silicon Valley. The reason I emphasize “real coaching” in this context is because until the client lands, my work with them is often more tactical—even transactional, although we start their job search and transition with a definitive strategy. But, once we agree on the message, targets, and on how to land a job the client does most of the work based on the plan we developed and asks for my help as needed. Of course, I help them during any glitches that happen during the interview and the selection process, and in negotiating their salary.
The real career challenges start surfacing after the clients start their new job and have spent about a month in their assigned roles. So, after the first month in their new job I work with my clients to develop a 100-Day plan to define their career path during their first year and then beyond. But, before we begin fleshing out the 100-Day plan I ask my clients these 10 questions that tell me how things are going and how they are going to go for there during the next year and beyond, and if they need to make major adjustments to their original plan to keep their career on track, including limiting their time in the new job, especially if the outlook does not look promising at that point; this is where you must know when to parachute out!
- What surprised you most in the first few weeks?
The reason for surprises during the first few weeks is the lack expectations management from both sides. During the interview process the employer showcases their best features of why the candidate should consider joining them. The candidate, on their part, does the selling, often over-promising skills, capabilities, and what can be delivered in a given situation. So, when the two sides come together as “the rubber meets the road,” there is often a mismatch of expectations requiring recalibration. Getting this fleshed out early from my client’s perspective allows me to help them recover their lost bloom, because, at this point in their engagement there is still time to recalibrate expectations and get back on track.
- What is going really well?
The energy with which the client responds to this question tells me how much to believe in their story. Really engaged clients aligned with their jobs are excited about the future and possibilities and cannot hide their excitement.
- What is going off track that needs immediate attention?
This is where we discuss the main players in the client’s new ecosystem and how my client’s relationship with its members is helping or not helping my client get good job traction. Even now, there is still time to do some repair/recovery work, but here timing becomes critical.
- What one thing can you do that will define your leadership in the next 3-6 months?
There are always exciting challenges in a new place of work. The new employee must focus on the most important and visible part of their assignment, so that if they succeed at it they will be held as a hero. There are ways to manage this success, so that your chances for new glory increase depending on how you set yourself up for that success early.
- Now that you know the place better, what is that you really want to be and do there?
A month is a good length of time for someone at a mid-level to get their bearings and to understand how the place operates that will allow them to flourish if they take the right initiatives to pursue, beyond merely taking orders. Helping a client navigate through this puts them in the driver’s seat to pursue their own path and to develop their own brand in a new setting.
- What are you doing well that is helping you get there?
Awareness of what is working and how to amplify that outcome leveraging what you do well is very important to keep building your brand and career momentum in your new place of work.
- What are you not doing well that is preventing you from getting there?
Awareness of the headwinds that are impeding your progress is also a good way to keep your progress on track and to make course corrections. In most cases these headwinds stem from poorly managed or assumed relationships.
- What will you do differently on your next day at work to change that?
This is the change that must come out of this assessment, so that the client can amplify the good and attenuate the bad.
- How and where can I help?
This is where coaching plays a part.
10. Where do you need most help (even if I cannot provide that help)?
If the client needs help in areas where there are commonly available resources (often free) I ask my clients to avail themselves of these resources to keep their growth on track.
The first few months in your new job are critical to make headway in how you position yourself for advancement and for building your career path. Becoming aware of what is really happening to you—the good and the unexpected—allows you to re-assess your strategy to keep your career momentum without impeding it. If you are in a new job, ask yourself these questions and find honest answers. You’ll soon see the benefits.
Good luck!

