Hannah Olinger via Unsplash

Oscar Health’s Sara Wajnberg on Asking More Questions To Change Team Behavior

Effective Leadership Series

Sara Wajnberg

As SVP of Product, Sara oversees Oscar’s entire suite of products including operational systems, internal tooling & doctor and member-facing mobile and web apps.

Sara spoke at our 2018 FirstMark CTO Summit alongside founders/CTOs from Doordash, Flatiron Health, Zenefits, Opendoor & others. We were so impressed with her leadership and vision that we were compelled to sit down with her to learn how she thinks about effective people management.

What was your first management role? What did you learn from it?

The first person I managed was a product management intern, and I remember how surprised I was by the amount of time I ended up having to spend with him. The biggest learning I had from that experience is that people management is very, very different from content leadership. Being a seasoned product person can easily translate into being a good product content lead, but good people management doesn’t necessarily come inherently and requires very different skills and training. Today, any time someone on my team expresses the desire to dabble in management, I make sure they understand that this is a very different function from what they’ve been doing, the switch doesn’t always work out for everyone, and it’s not the only path forward to growth — just to make sure they’re really ready for it.

Good people management doesn’t necessarily come inherently and requires very different skills and training.

Early in your career, before you assumed leadership roles, what was one quality you appreciated in a great manager?

Advocacy. The managers I most appreciated were the ones I felt had my back and would go to bat for me — help me out when I needed something to be more effective at my job (e.g., access to production data!) or had a conflict that I couldn’t resolve on my own. Lack of action for me bred mistrust and disillusionment, so those managers that took my frustrations and concerns seriously and actually did something about them were the ones I most wanted to work for.

Is there one moment you can point to that fundamentally shaped your approach to leadership?

I went out on maternity leave and left my report to fend for himself in my absence. When I came back, he was disappointed — he had enjoyed having more visibility and responsibility while I was gone and was worried that my return would result in things getting worse for him. This was a real shock to me. That experience made me realize that I never wanted my presence to hinder a report’s growth or success, but instead I wanted to help enable them to live up to their full potential. I started working on delegating more effectively and giving my reports autonomy, and haven’t looked back.

I never want my presence to hinder a report’s growth or success, but instead I want to help enable them to live up to their full potential.

What are the most important daily or weekly habits that you’ve developed as a leader?

One thing I have found invaluable is to regularly pull up my org chart and go through every individual in my mind to make sure they’re getting what they need from me/my reports, that I know where they stand and what we’re working on to develop them, and that I have a good read on how they’re feeling. That continuous mental touchbase often allows me to get ahead of things before they start burning.

What framework do you use for your one-on-one meetings?

My approach to one-on-ones is pretty personal, starting from the amount of time and cadence — I try to let my reports figure out what amount of time they want from me and how often we should meet, and adjust as needed as time goes on.

For one-on-one frequency, it varies:

  • 2x/week for a half hour each time (sometimes one tactical, one career-oriented session),
  • some only 1x/week for a half hour,
  • some 1x/week for an hour, etc.

As for topics, we always start out by setting an agenda together.

The one-on-one agenda covers:

  • what does the person need from me,
  • what issues are they dealing with that I can help them resolve,
  • what topics are brewing that I should be helping get ahead of,
  • what information do I need to give them to help them be more successful, etc.

We real-time prioritize the topics (because time is always more limited than you think!) and I keep close tracks of follow-ups expected from each of us so we can make sure we take action afterward. I also like to occasionally get out of the office into more informal settings to pull up and discuss how things are going and how they’re feeling about their time and trajectory with the company.

What is the best approach you’ve used to help change team members’ behaviors?

I have a well-earned reputation for asking a ton of questions. Sometimes this makes people who aren’t used to working with me feel as though I’m questioning how prepared they are or whether they’ve thought through something fully, but I am usually just genuinely curious and feel as though I can’t really weigh in on something if I don’t adequately understand it.Asking lots of questions often reveals that someone has made assumptions they still need to validate, or that they don’t have the answer to something that probably will be asked of them. My goal in doing this, beyond improving my own understanding, is to help people learn how to get the full picture of a problem before forming an opinion or designing a solution, and I do think that this style of interaction helps train people to do that more naturally. I apply the same methods when talking about less tactical things like cultural concerns or questions about career pathing; asking lots of questions allows someone to sort through and better understand their own thinking, as well as consider other perspectives.

Asking lots of questions allows someone to sort through and better understand their own thinking, as well as consider other perspectives.

What advice would you give to a first-time manager about giving effective feedback?

The best advice I could give for new managers is to try to write things down — and get a second set of eyes on it! — before you go into a session where you’re planning on delivering feedback. If you’re not prepared, you can find yourself fumbling live and risk either not delivering a clear message, masking the severity of the problem because you feel bad, or finding yourself backed into a corner and defensive. Take the time to think through the framing of your feedback and how you want to deliver it in advance, and get help from someone you trust! Once you’ve practiced this enough times, it’ll become more natural for you to do it effectively off the cuff without as much preparation.

The best advice I could give for new managers is to try to write things down — and get a second set of eyes on it!

Have you worked with a coach, and if so, what was the biggest lesson you learned?

I haven’t worked with a formal professional coach, but we do have a function at Oscar called People Strategy (similar to the role of a traditional HR business partner, but even more expansive), and I am paired with someone that is essentially a coach who has had a huge impact on my thinking and on my career development. The biggest lesson I have learned from working with her is that I have subconscious mental blocks and insecurities that prevent me from proactively stepping up to take on broader roles and responsibilities. Each time I’ve progressed roles and become more senior it’s taken months to build up my confidence and get myself into the right mindset, but it’s definitely getting easier the more I’ve internalized and recognized that this is a gap that I have to work extra hard to overcome and that I usually do just fine after I’ve gotten over the mental hump!

Oh, and I talk too fast. :)

What’s one thing you are working on now?

One thing I’m working on now is helping the team achieve a better balance between long-term vision brainstorming and articulation vs. day-to-day execution against our nearer term objectives. We are doing a lot, and sometimes it feels as though there isn’t enough time to think far ahead. We’ve already put some mechanisms in place to help get us in the right mindset (such as healthcare tech strategy sessions every few weeks, regular strategy offsites, newsletters we all subscribe to, etc.) but we still have a lot of work to do to achieve a healthier balance between the now and the future.

Thanks for sharing, Sara!

Want more? Read Sara’s recent post (below) for more on her current focus.