Menu
fist

Q&A with Anna Rappaport

I was happy to meet and talk with Anna Rappaport at a happy hour in the fall about her work as a career coach.  I had not worked with a coach before and was curious, as a few of my friends had great things to say about their experiences.  I also thought I could improve my efforts to generate business, so I reached out to Anna for advice.  We reconnected a few months after our coaching session, and I was excited she agreed to be interviewed for Shattering the Ceiling.

Kate

During our coaching session, I talked about my broad goals, and you guided me in making them much more specific and concrete.  You also asked me to envision what success would look like and to imagine how I would feel after successfully meeting my goals.  Can you talk with me about these two coaching strategies you used and about what makes them effective?

Anna

The visioning and specificity help clients both with motivation and with making good strategic decisions. I’ll address motivation first.  Making our goals specific and concrete makes them seem more real.  Rather than an abstract dream, it becomes a viable plan, with clear action steps. When we see a clear path that could realistically lead to success, we get more motivated.  Similarly, when we envision what success looks like—really imagine what our lives would look like if we achieve the result—we get more inspired, excited and motivated to achieve that goal.  Starting with a vision for success also helps clients make good strategic decisions because they have to explore their own reasons for wanting to achieve that goal. Two people could want the same exact goal, for example, to become a partner or CEO, but their reasons could be quite different. Getting clear about the underlying intentions helps ensure that people are choosing goals that are a good fit for them.

Secondly, the more specific we get in the planning process, the more we think through how the actions fit together, the timing, and who else should be consulted. A plan never goes exactly as we design it, but planning making us consider options and approaches in a systematic way that leads to better strategy and speeds up the results. Also, clarity about actions, milestones and deadlines helps us to be honest with ourselves about if we are on track and if we need to shift our behavior or plan. It helps us to hold ourselves accountable as we strive to implement our plans.

Kate

In your experience, what are the biggest pitfalls that you see women facing in their careers?

Anna

Everyone gets stuck sometimes. It is normal that this happens occasionally in the course of one’s career. However, it becomes an issue when we interpret our lack of success in particular circumstance to mean that a person, relationship, or situation is hopeless. It is the resignation and hopelessness that is the pitfall.  Even though being stuck can feel pretty lousy, it is actually an opportunity to acquire a new level of wisdom and competence.

Kate

In what ways do you see often women getting stuck?

Anna

Women usually come to me with questions about how to deal with some aspect of their careers, such as how to delegate more effectively, manage client demands or get more clients through networking. Finding good advice for such questions is not difficult in the age of the Internet. However, actually applying that information in one’s own life can be challenging. As women, we tend to be more sensitive to all the different factors affecting relationships and communications and can easily get caught up in a whorl of theories, hypotheticals and extenuating circumstances. Nevertheless, despite all the apparent complexity, most of the time, it is our underlying beliefs about ourselves, other people, or the world that are the real issue.  When we recognize the belief that is holding us back, we can address it and move forward far more easily than we might imagine.

Kate

Can you give us a couple of examples of this?

Anna

One client, let’s call her Jennifer, knew that in order to develop business it would be smart for her to reach out to her former colleagues from when she worked at large law firm.  But she really didn’t want to.  When we explored further, it became clear that the real issue was that she had always seen herself as the odd one out, like she has never fit in, and felt uncomfortable reaching out to those who she more or less perceived as the “cool kids.”

Mary provides another example. She reached out to me because her managing partner told her that she was not aggressive enough in developing business. Quickly, it became clear that her default approach to challenges in life was to gather as much knowledge and expertise as possible before moving forward. This is a fantastic quality in many ways and led her to become an excellent lawyer.  However, it was an impediment in terms of business development because she avoided selling herself and her firm to potential clients if she didn’t know absolutely everything about whatever esoteric issue they were confronting.

Kate

As an employment discrimination lawyer, I need to chime in here to note that I also work with women like Jennifer, who are not among the “cool kids” (or “boys clubs,” as we often call them), and Mary, who is criticized for not doing more to develop business.  I see that biases in the workplace often exclude women from “in groups,” and that membership in these groups often provides networking and information necessary for business development.  In my work, I talk with women like Jennifer and Mary to identify the barriers they face in the workplace and to hold companies accountable.  It sounds like you work with women in similar circumstances to help them identify barriers that they may be imposing on themselves.  Can you talk about how coaching helps here?

Anna

We all have underlying beliefs that drive our behavior. “My work must be perfect.” “I don’t fit in.” “Knowledge is the answer.” “People can’t be trusted.” “People who stand out too much get crushed.” Beliefs like these may serve us well for some period of time, but as we move forward in our careers eventually we get to a point where they limit us.

Coaching helps people take their lives from good to great, or from great to off-the-charts amazing.  It is forward-looking, and it involves designing projects and taking actions.  We identify a limiting belief, and we address it as an obstacle in the way of achieving greater success or satisfaction. We don’t spend a lot of time dwelling on the origins of these beliefs or who is to blame. What I have always loved about coaching is that it can be very quick.  People can shift their perspective much faster than most people imagine and this can lead to previously unprecedented results.

Kate

What are some key strategies you find yourself regularly proposing to women?

Anna

Coaching is totally individualized, and I draw on a wide range of approaches, but like we already discussed, planning and visioning are both important tools.  I also frequently encourage people to step outside their comfort zone and take risks.

Kate

Can you talk with me about the value of taking risks?

Anna

Much of what stops people in life is fear.  By having conversations that feel risky or taking on new challenges, people are able to increase their confidence. People start to recognize that even if something doesn’t go perfectly they can still handle it and be okay. Building this faith in oneself has all kinds of benefits in terms of trusting oneself and creating opportunities.  This also comes with a greater sense of ease and fun in life.

Kate

Can you give me an example of how you work with people to take risks?

Anna

I often encourage clients to ask for feedback from at least ten people, including friends and family as well as from work colleagues and clients. I have a series of questions that I recommend they ask, which can be used to seek an honest assessment of their strengths, weaknesses and how they come across.  That feels like a huge risk to most people, and some are really reluctant to do it.  But the people who do it find it very helpful not only because having those conversations gives them more awareness and deepens the relationships with the people they talked with, but also because it builds up their “bravery muscle.”

Kate

One last question, on a more personal note.  Can you talk about what makes you successful as a self-employed coach?

Anna

My advice to people wanting to go out on their own is: just keep at it.  Don’t stress when things don’t work out as quickly as you would like.  As the start-up community says, “fail fast.”  Everyone makes mistakes. It is inevitable.  Rather, the goal is to learn from everything you do, both the successes and the failures. That is what allows you to become the kind of person you want to be and create a career that you love.

*  *  *  *  *

I enjoyed my conversations with Anna, and through a coaching session with her I learned there is a lot more I can be doing to meet my own career goals.  For more information on her coaching, check out her website here.  I think there are a lot of benefits in identifying the barriers we may be facing and to doing what we can to remove the barriers we create for ourselves.  I also know from my work that some employees – women and people of color in particular – face more barriers than others, and that these barriers are not of their own creation.  For more information on my work representing people who face those barriers, check out our firm’s website here.

Kate Mueting

Kate Mueting

Kate Mueting dedicates her working hours in the DC office of Sanford Heisler, LLP to advocating on behalf of women and to speaking on issues of pay equity and gender fairness.  Because she cares about it a ton, Kate also manages to talk about gender equity during non-working hours, although this is liberally sprinkled with references to her home state of Iowa and to her selection as Rookie of the Year by Nebraska’s marching band. 

shard4 shard5 shard7 shard9 shard10 shard11