CEO Learnings

5 Business or Pleasure Tips

June 11, 2019
  1. BE A MERCENARY / MAKE YOUR PRIORITIES LOUD & CLEAR

    Let’s say you want to be a founder. At InDinero, our first group of salespeople became founders themselves, and I knew that was their dream from the start, so we designed work experiences to help them learn the right skills. You can say, “I will work as your VP of Sales and ultimately I want to be a CEO one day.” Sometimes, people, women especially, aren’t used to doing this. “But Andrea,” you may ask ”...aren't I supposed to say I want to work for you forever and ever?!” If I had an amazing hire on the table who was clear about an ultimately divergent career path, I may still hire them with clear expectations about the mutual benefit we’ll create in the meantime.

    Same thing on the pleasure side. For example, I tell people I date right away that I don’t want to get married again. Sure, that filters some people out - but it’s better to communicate my needs up front and save everyone’s time.

  2. NEW RELATIONSHIP ENERGY

    Whether with a new partner or with a new hire, take it slow, set clear expectations, appreciate the excitement of the honeymoon period but remind yourself that there are no perfect humans in this world, including ourselves. When everything’s rosy and perfect, the first fight or moment of tension can make you question everything. Are we meant to be together? Is this person the right fit for the job?Breathe in and breathe out. Those first hard moments do NOT mean you’ve made a huge mistake. Keep going and know that whole humans are stronger and more valuable than our brittle, perfect images of them.

  3. MEDITATION & MINDFULNESS

    In a surprise to no one, I am a Bay Area startup founder with a meditation practice. My practice has helped me ride the waves of both business and love, but you don’t have to sit on a cushion somewhere to work on gaining a bit of peaceful acceptance. Accept the idea that there are a lot of relationship styles and work styles, and that your job isn’t to change your partner or business partner; it’s to find one whose strengths and weaknesses complement your own. Finally, implement systems and communication that will help you fill in the gaps, because there will never be a perfect fit.

  4. MEASURE ACTIVITIES, NOT OUTCOMES

    “I just want you to...be a better partner.” Seems like a terrible way to get something to change in your relationship, right? If someone said that to me, I would a) feel sh*tty about myself and possibly defensive, and b) have no idea what they actually want me to do.

    My #BusinessOrPleasure lesson is that at work and in love, you gotta focus on activities, not outcomes. “Be a better partner” is bad direction, but “It would make me feel good if we had dinner two or three times a week without our phones” is clear and measurable. Equally, it’s less effective to tell a salesperson that they HAVE to close $100,000 worth of business per month. It just doesn’t work that way. But I can make sure they’re doing 100 sales calls a week.

  5. KEEP WORKING ON YOURSELF

    In business, sometimes managers hesitate to invest in developing employees – i.e. spending resources or time on additional training & leadership opportunities. But I really agree with this maxim: “What if we develop our employees and they leave? What if we don’t, and they stay?”

This is one of my favorite #BusinessOrPleasure lessons that I see so many parallels with in relationships. So often around me, I see one partner in a relationship get complacent – and it’s on them AND their partner to avoid getting the both of them stuck there. It doesn’t have to be career success, but I strongly believe partners should continue to seek personal growth, and to challenge each other to do so, as well.

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