Career Guidance with Robyn Rapp

Tips from a partnerships exec turned career coach

As we approach a full year of life amid this global pandemic it is impossible to avoid dreaming about life on the other side.  What will it feel like to hug my mom and dad?  When will my first in-person meeting be?  How long will it be before I can meet a friend for a drink after work?   For so many, the pandemic has meant a long list of personal and professional challenges.  And for some, that list has included a career setback.  A promotion postponed.  Or a startup that wouldn’t start.  In this way, the end of the pandemic will also mark the beginning of a long-awaited job search for some.  That is why I reached out to Robyn Rapp who, after more than 15 years in a collection of sales / business development / partnership roles at Google and Slack, launched a business as a career coach.  Robyn brings her unique perspective managing her career and managing teams to help executives figure out their next career moves.  

A few example insights from the interview below: 

• “If you’ve settled into a career without zooming out and thinking about who you want to be and what’s important to you, you may very well find success in your chosen path but you may not be chasing actual happiness.” 

• “Don’t start your job search until you start your soul search. If you start with LinkedIn for your search, it’s unlikely you’ll discover the magic of who you are and what you yearn to do.”

• “I see myself as a personal and professional development coach and don’t see a way of decoupling the two, I would suggest getting a coach if you want more out of your life, if you’re feeling stuck, blocked or uninspired.” 

Before career coaching - partnerships @Google @Slack

Can you share a bit about the work you did at Google and at Slack? 

I started off in the ads world back in 2005 when Google was primarily a search engine, fueled solely by ad revenue and spent the bulk of my time at Google post-MBA in Business Development, cultivating partnerships with retailers and financial institutions in the Google Shopping, Commerce and Payments teams respectively. 

How did you find the approach to partnerships differed at Google vs. Slack? 

Partnerships at Slack looked quite different than at Google, at least in my experience. While partnerships at Google required heavy lifting in terms of contract negotiations and resulted in consistent product integrations across retailers, Slack partnerships with B2B Saas providers, esp in the early platform days, were very much product-led, void of heavily negotiated contracts, if any, were far more bespoke and varied greatly in terms of marketing activities and implementation.

Part of that difference in approaches stems from what value these partnerships were attempting to drive. Given that the Google partnerships represented direct incremental revenue, discussions often anchored around ROI and rev share.

Because the Slack platform wasn’t monetized, the true aim of the partnerships centered around the end user experience, including improved efficiency, productivity and the reduction in context switching. The aim of Slack partnerships was to make Slack and our partners’ software that much more useful, stickier and powerful as a result of the integration, resulting in better customer retention and in some cases, increased customer acquisition. 

Also due to the maturity of Google relative to Slack when I joined, Google’s product integrations tended to be fairly binary and non-negotiable - either you plug into our APIs in this fashion or you don’t. At Slack, the possibilities of how our products integrated with one another was endless. As such, my creativity was cultivated throughout the process of identifying what might be possible to accomplish together both from a product and marketing perspective. It was pretty energizing leading design workshops and working hand in hand with product managers and engineers on beta launches. 

What was one big lesson you took away from doing partnership deals at Google?  At Slack? 

Know when to hold ‘em and know when to fold ‘em: Make it clear through your actions that you’re invested in the partnership, underscore what you and your partner stand to gain by collaborating, and move mountains to create and sustain the momentum to get it across the finish line if you truly believe that it is good for all parties. 

On the other side of the coin, it’s equally important to know when a partnership is not worth pursuing. Imagine the opportunity cost of executing against this partnership. Are you neglecting a truly valuable partner just to save face, to justify the sunk cost of 6 months of unfruitful discussions, or simply clinging onto the sexiness of a partner’s brand? If so, cut your losses and move on to something that is truly worth your time and effort. 

As you look back on your own career in partnerships, what is one thing you think you did effectively in terms of your own career development and what’s one thing looking back you realize now you should have done differently? 

I established trust quickly and maintained authentic relationships internally and externally. As a new coach, I’m seeing those former colleagues and partners continue to help me find my footing, offer sage advice and have been responsible for a consistent flow of new clients to my practice. In fact, I’ve now coached several former colleagues and I’m surprised at how seamless it has been to wear the coach hat vs friend hat during our sessions. 

As for what I’d do differently, man, how much time do you have? In all seriousness, I realize that I played it safe... a lot. I wish I had taken more risks and been more comfortable with missteps and “failures” if it had meant getting more of my ideas and contributions out there. This notion of playing it safe and needing to know something backward and forward before I voiced an opinion, i.e. perfectionism to a paralyzing degree, is something I see in many of my female clients. I’m very devoted to helping others find their voice and the courage to take risks. 

Career guidance

I think there's a large portion of This for That readers that are thinking about making a job change after we emerge from this pandemic / economic downturn.  What advice do you have for them on how to make good use of the time before beginning an active job search? 

Don’t start your job search until you start your soul search. A true search may involve the following:

• Start making a list of what you care about. Where does your brain naturally wonder? What are you constantly posting about on social media or soliciting your friends opinions about in discussion? What keeps you up at night?

• Who do you wish to serve, impact or uplift?

• Who are you under optimal circumstances? What gets in the way of you being your best self? 

• What have you been tolerating that you wish to eliminate in this next career? 

• What are your top values and priorities? 

  • Trade offs are almost always necessary when pursuing your dreams.  Making sure you’re making the right trade-offs and not sacrificing the things you truly need in your life is imperative. You can’t have 10 values guiding your decisions. At that stage, your values don’t inform your decisions but rather paralyze you from making any. Whittle it down to the top 2 to 3 priorities max.  Figure out what’s most important and guard it with your life. 

What are some of the most common mistakes you see people make in their job search? In interviewing?

Their search is reactive, safe, familiar and uninspired. If you start with LinkedIn for your search, it’s unlikely you’ll discover the magic of who you are and what you yearn to do.  Many people are often well aware of what they’re running from but haven’t yet reflected enough on what they’re running to or who they’d like to become. 

As for interviewing, less seasoned professionals tend to forget their own power in the interview process because they are not grounded in the value they bring to an organization. We should all be aware of our superpowers and gifts. Interviewees should bring an equally critical, curious mind to the interview and remember that both sides are determining if there is a good fit. 

Beyond just job searching, what are some of the most common career mistakes you see people make? 

I see people who are desperate for change and uninspired, yet play it safe when it comes to what they’ll consider next. They also tend to look at their next job as the end all be all but it is just a step. At the very least, it is movement away from the known thing that isn’t bringing you joy or fulfillment. There is no such thing as a mistake. It is simply part of your journey. If you don’t like where you land, it’s time to consider the next step. Baby steps towards what you want are still steps. 

Many of the requisite skills in technology partnerships roles are primarily collected via experiences, like leading a team, owning a large, complex deal, scaling a business.  Given this, what is your guidance on skills development?  

Observe, network internally, and get involved in side projects to gain an understanding for how your business works more holistically. From there, take inventory of which skills and roles are of interest to you and how they might propel you into something more fulfilling or interesting. Often getting exposure to desired skills is easier in a place where you already have a brand and a proven history. 

Alternatively, getting an advanced degree, such as an MBA, or taking a class such as coding bootcamp signals to the market that you’re putting in the work to understand some of these skills at least at a theoretical level. Mustering the motivation to stretch yourself may also be more feasible after reflecting upon how much you’ve already learned to date and what a thrill it can be to increase your knowledge and skills set. Even if it’s remembering how cooking used to terrify and intimidate you and now it brings you great calm, it is important to remember that it’s never too late to learn something new. 

If you could take your clients back in time and tell them one thing to help guide them in their careers, what would it be? 

Think about yourself on your death bed. What would she tell you to care about and pay attention to now? Remember that career is simply one of the many vehicles available to us to express ourselves, to leave a legacy, to nurture our strengths and interests, and to lead a life of purpose, happiness and fulfillment. If you’ve settled into a career without zooming out and thinking about who you want to be and what’s important to you, you may very well find success in your chosen path but you may not be chasing actual happiness. 

What is one belief about career development you previously held but has changed since you became a career coach?

I used to think that a coach solved problems for you, but that’s more the role of an advisor or mentor. Now I appreciate how important it is that a coach simply provides the time and space to reconnect with yourself, establish unflappable confidence, redefine success in your own terms, hold you accountable and ensure that you tap into the wisdom and clarity that you already have. 

What is a career coach as you approach the role? 

I see myself first and foremost as a self-actualization coach, as someone who will walk alongside clients to help them develop and evolve as human beings. I first help people identify who they want to become, the legacy they want to leave and how they want to feel and make others feel around them. Everything else is secondary, career included.

By establishing the biggest, brightest version of themselves as the north star, it is far easier to then align the career, philanthropic activities, self-care regimen, relationships and extracurriculars that will support the pursuit of who they are becoming. 

I hold space for clients to reflect and to be acknowledged and celebrated. My only agenda is to uphold their agenda. I will remind clients of what’s important when I see them deviating from their north star. I will encourage follow through on what they deem is important and will call them out when I see them doing things for optics, or because of external pressures that often contradict with what they truly want. I help clients translate insights gleaned in our sessions to actionable next steps and deepened learning to ensure that there is constant progress, movement and growth. 

When do you recommend a professional should enlist the help of a career coach? 

Since I see myself as a personal and professional development coach and don’t see a way of decoupling the two, I would suggest getting a coach if you want more out of your life, if you’re feeling stuck, blocked or uninspired. A coach can help you reconnect with yourself, override that boisterous inner critic, challenge you to dream bigger, and help you define success in your own terms instead of everyone else’s and then pursue those dreams with intention, focus and clarity.

What is the typical profile of your clients?

At this early point in my career as a development coach, I don’t actually have one. I work with men, women, and LGTBQIA. Clients are orthopedic surgeons looking to get out of medicine and tenured attorneys in the public sector looking to get into the private sector, hoping to reclaim a life outside of work that has been shelved for far too long. 

I work with those that are waking up to the reality that they’ve been doing what they felt like they should do instead of what they want to do, often the result of societal and cultural pressures.  Many battle imposter syndrome, harsh inner critics and saboteurs. Seasoned tech executives approach me, yearning to do something that aligns more with their values, such as contributing to socially responsible media or solving the affordable housing crisis. Most want to rely less on external validation and move away from perfectionism. Several clients suffer from limiting beliefs and fixed mindsets. I’m on a mission to help my clients understand the power behind a growth mindset and the reassurance that we can all adopt and embrace one if we so choose. 

I very much appreciate and feel energized by the broad spectrum of professionals I’ve coached with respect to industry, tenure, seniority and functional roles. 

How would you suggest someone select a career coach? 

This is an intimate process. Honestly, it is the biggest privilege to have clients share their vulnerabilities, dreams and hopes with me and I believe the only reason that occurs is because of a high degree of trust. There are many coaches out there with incredible accolades, training and backgrounds and that is wonderful. At the end of the day, however, if you can’t open up to your coach, you are going to leave a lot of growth potential on the table. Go with your gut, share the full range of who you are and find someone that puts you at ease.

You can learn more about Robyn’s coaching practice at https://robynrapp.com.