In my life as a manager, a leader, and a coach I’ve been frequently asked for help or advice about the next career steps. In my life as an employee I have frequently faced the same questions from myself and not always had a good answers. So what do you do when a team member or a coaching client comes to you and wants a piece of advice? Whatever you do, don’t give it! Each of us has different values and different goals in life. Each of us is at different stage of our careers and due to different skillset have also many different options of what to do.

So instead of providing answers start asking questions. Especially in a coaching relationship it is always a good idea to start with the big picture and talk about the value system, and the non-professional part of life to ensure that the work piece fits nicely with the rest. To guide you through the career coaching session let me share couple of questions that may get you started.

Who are you in your professional life?

It is good to define who the person is in his professional life and who he wants to be. It should provide high-level framework for the rest of the discussion.

• What are the things you like in your work? And why? (You have to ask this but don’t expect any deep thoughts, it is essentially an ice breaker.)
• What are your strengths? (Forget about weaknesses.)
• Why do you work? What is your motivation? (And don’t say money, dig a bit deeper here so you find the real drivers.)
• What are the skills you are learning and you want to learn? (Most people have some things they would really like to learn and usually there is a deeper reason behind.)
• What are the skills you need to learn? (Most likely set of skills you are missing to outperform at your current level in your current job.)
• What is your dream job and why? (This may lead back to values and should help to identify whether the person is actually in the right field and shouldn’t make a bigger change to be happy.)
• When was the last time you were “in the flow” and what were you doing? (You dig deeper here to understand what are the things that make this person go above and beyond.)

I personally just love asking these two questions. In fact I love them so much that I tend to ask them even in interviews when search for leadership potential. I believe that because they require a very succinct answer they push the person to think a lot about who he really is and possibly who he wants to or how he wants to be seen in his professional life

• What is the mission of your professional life?
• How would you describe yourself on twitter (140 characters or less)?

To give you example I just returned from my Philippine mission back to Europe and found many new faces in the office. Instead of giving these new team members the whole story of my life I decided to make it twitter like “I’m the guy who builds offices and grows people” (in fact only 47 characters including spaces). This essentially sums up the last six years of my professional life and that is how I see myself and would hope that others would see me today. Is it how I want to be seen for the rest of my life? Most likely no and when I get tired of this particular picture of myself I will come up with a new “mission” and then will try to find a job that will fit this new image of myself.

How are you seen by others?

You need a sanity check so answering this question would really help and to make sure you get an honest picture you probably want to ask around for some feedback

• What feedback do you have from others?
• How are you seen by your bosses, peers, subordinates, and partners?
• What are the things they are saying that are not in-line with what you believe about yourself?

What do you keep and what do you lose?

Now, let us talk about what aspects of your job you want to keep and what you want to get rid of. For example, I hate dealing with bureaucracy so I would try to set my job in such a way that I don’t need to deal with it too much. Or I just love working with people so whatever my next gig is it has to have a strong aspect of working with others.

• What are the key aspects of your work you want to keep?
• What are the key aspects of your work you want to change?
• What is standing in your way to get your dream job? Any skill gap? And if yes, how do you plan to tackle it?

What is out there?

The philosophical part is behind us and now to a real field work. These questions are just to guide a person but most likely cannot be answered in the first coaching session. It can be a good idea to ask the person to do his homework and research a bit what is happening around him. Starting with how his colleagues work. Why are some of them happy, what drives them, what are the opportunities inside the company and what is the situation on the job market? Depending on the results of this search you can continue with some of these

• What realistic opportunities are out there for me? (The key word is “realistic”. If you are a fresh manager with two months under your belt you can hardly expect to get a fancy job of a director responsible for bunch of teams around the world. At the same time don’t let the titles fool you. Each company has a unique way how it is structured and depending on company culture, size, and maturity the titles may vary quite a bit. So instead on headlines focus on job descriptions.
• What can you do to increase the number of these opportunities? (Would training help? Contacts? International experience? Etc.)
• How can you learn about them? (Do you need to do something proactively?)
• How can you let others know that you are a suitable candidate for these roles? (Be creative and think long-term. Do you join some professional association? Do you start answering questions on some industry related public forum? Do you seek opportunities to help out your colleagues or people from other departments? Do you start building a network of contacts within your industry?)

How do you select the right opportunity?

At this stage you should have a pretty clear picture about what is out there, what your values and skills are and what positions you believe are a mutual match. The worst thing at this stage that can happen is to have more than one option to choose from.

• What are the key criteria to help you decide what is the right opportunity?
• What are the things you are willing to sacrifice in case of really interesting opportunity? (And believe me you need to be able to make sacrifices. There is nothing on this world as a perfect job. At least not at the beginning. To have a perfect job you need to step into one that is relatively close and then mold it and let it mold you in such a way that one day you find you and your job be the best friends)
• Who will I ask for an opinion? Who are the people I trust to give me a good advice? (This one might be important question. Who are the people impacted by your decision so you want to give them a chance to voice their thoughts? Who are the people you value for their wisdom and life experience? Just remember at the end of the day it is your decision and you will have to live with consequences.)
• How will I know I made the right decision? (You won’t until you make the choice and live it out. It might be a good idea however to have some sort of success criteria defined that you can consult in couple of months to see whether the change you made had the effect you desired.)

How do I start?

If your coaching session wasn’t just a theoretical exercise but you want a real change then it is important to define some plan and the first steps to get things moving

• How well are you prepared for job interviews? What can you do to improve?
• What are the first steps you need to take?
• What are the results so far and how can you improve them?

Twitter type summary: “To help others find their place in the world you need to be unbiased and ask the right questions that will struck deep into who they are.”

What are your favorite questions you use to stimulate others to plan their career? Are there questions you would never ask?

Photo: Shutterstock, Inc.

Categories: Career, Coaching

Tags: Career, Coaching