Improving Your Odds of Career Success

A framework for ‘selling’ yourself and getting paid your full value

“I have never worked a day in my life without selling. If I believe in something, I sell it, and I sell it hard.”Estée Lauder

Selling is an undervalued skill. The most successful people (almost regardless of field) have developed strong selling skills out of necessity.

Why it Matters: Our careers involve a lot of ‘selling’. Much more than we imagine when we enter the workforce in a non-sales role.

We sell to get the next job or promotion, to be included on the coveted new project, to raise capital and keep the business afloat, to convince people to join our organization, and to earn the trust of team members.

Elements of Successful Selling: The likelihood of success in your career increases when you leave every sales interaction having conveyed the following:

  • An Understanding of the Business and Customer Problem(s)
  • An Ability to Reduce Risk
  • That You Are Trustworthy
  • And Are Likable


Diving Deeper on the Elements of Successful Selling

An Understanding of the Business and the Customer Problems

After listening first, demonstrate that you understand their problems. The key is asking the appropriate probing questions which demonstrate your understanding and push them to disclose more about the desired outcome.

Offer a plan or a diagnostic process to address their concerns. Uncertainty and fear go down when the buyer feels the other side has a realistic, thoughtful approach to problem solving.

Be willing to give them something for free. Your ideas on how to solve the problem are only a small portion of the solution. Execution is much harder. Share your ideas readily.


An Ability to Reduce Risk

The most common outcome in a sales conversation is inertia and inaction. No one gets hired and the job remains open. No new solution is implemented. The status quo persists.

The fear of making a mistake (in hiring) or ending up with an implementation nightmare is front and center in the mind of the buyer. 

You need to convince them that your proposal is low risk and high reward. This is where a trial period (for work), a proof of concept or an early termination right can be highly valuable. 

Point out that you will take initiative to solve the problem and don’t have to be told everything to do. And at the same time you will seek their input on important matters.


Are Trustworthy

We are programmed to distrust sellers. There is always an asymmetry of information between two parties in a negotiation. Each side knows things the other does not and often is unwilling to share openly.

To earn trust, provide social proof. Go beyond LinkedIn reviews or the ‘average’ customer stories. Offer introduction to relevant references, especially people they might know (directly or indirectly.) If you have sold to / worked customers in the same vertical or business model, point that out. References are much more powerful when coming from people with similarities to the buyer.

Do your best to showcase how your incentives are aligned. That their success translates into your success. Offer to refer them to others if you don’t think you are their ideal candidate for all their needs, today and in the future.


Are Likable

People work with and buy from those they like.  And feel some personal affinity for. Do your best to build a personal connection without sounding fake or forced. 


Additional Ways to Strengthen Your Pitch

  • Differentiate yourself through intangibles. Talk about your working style and approach. How you solve problems, especially when the appropriate answer for their situation isn’t obvious or known.


  • Understand the perspective of the other person. Convey clearly that you can anticipate their objections and concerns. And are willing to address them directly.


  • Volunteer your weaknesses. You (as a potential hire) or your product (as a potential solution) are imperfect. In addition to your strengths, lay out situations for which you are not the best solution. That level of honesty is both rare and refreshing.


  • Assure others that you will be there with them from beginning to end. If needed, in the weeds, all the way through to a solution, addressing unexpected challenges that arise.


Pick up tips by watching and listening to others who excel at sales. Incorporate those that fit with your personality into your sales pitch. Like most everything else, being great at ‘sales’ requires a combination of continuous learning, thoughtful practice, and making it into something you like doing.

Aditya Dehejia

Adi’s experiences as a CFO and HR leader in start-up companies inspired him to start the CxO Leadership Accelerator. He saw firsthand the challenges in building a satisfying career, the importance of leaders in developing people, and the difficulty in building broad business acumen while excelling in your functional role. Prior to his operating career in start-ups, Adi held roles in a growth capital investment firm and in the corporate development and strategy department at a Fortune 500 company. Adi is an active volunteer mentor in the FirstRound Capital and TechStars networks as well as within his University alumni communities. Adi was born in India and immigrated to the US at age ten. He attended Princeton University (graduated with a degree in Politics) and the Stanford Graduate School of Business. He lives in the suburbs of New York City and has two adult sons and two lovable, crazy dogs.

Leave a Comment