Coaching files: How to stop being typecast

I had two pro-bono coaching sessions with BigShyft today as part of their charity initiative for COVID-19 relief. It was a gratifying experience - I wanted to briefly share one of the stories here.

P is a business analyst / program manager with 12 years of hardcore domain experience in a specialized sector, with a long time at a single MNC.  He wants to move into a primarily leadership role and for the right reasons: He is fulfilled by fostering the development of his team and he wants more say in strategic decisions.

But he's not getting that. So we looked at two avenues he has laid out. Both topics deserve posts in themselves,

  1. How do you change domains when your network is very limited and your expertise is very specific? Who will give you a chance and why?
  2. What's stopping you from getting trust of management to grow your span of control in your current organization?

In his case, for #1, we talked about several behaviors that can be effective:

  • Be more specific in your interest and shout it out to anyone who wants to hear it. Asking people for connections does nothing, asking people for a connection to a specific individual or a specific company, or an informational interview can open doors and build relationships
  • Network with public figures too. Follow people in the domain you are interested in, or from your skillset on twitter, linkedin, etc and interact with them on their content.  You'd be surprised how accessible so called "celebrities" are if you're authentically engaged and not self-serving in your interactions.  These people, but more importantly, their communities can open doors and open your mind.
  • Get used to rejection.  People use biases to take quicker decisions. Those biases are largely ineffective but they are there.  There is the college name bias (if I had an IIM degree people would listen to me) and there is the domain bias (this person will take too long to ramp).  Yes, they are more often wrong than right, but you can't fight every battle.  Just keep reaching out.

On the 2nd one, we spoke about his challenges to grow within the organization from a leadership (as opposed to a technical) angle.  When we started the conversation he said to me "It's really a privilege to talk to a CTO of a big company, I would never get this chance in my organization."  To which I replied: "Have you tried?".

Most of the time, we sell ourselves short.  And the best leaders are the ones which don't seek power for power's sake and they often are left by the wayside as a result.  Sadly, this can concentrate big egos and borderline sociopaths in senior management, but it doesn't have to be that way.

I asked him if he has explicitly laid down his intentions to his manager and asked for a plan.  He had not as "my manager is fairly new, and things change a lot here, so it doesn't seem like the right time."

It will never be the right time for an organization to take care of you.

Organizations are intrinsically designed to serve themselves.  Accept this, and be specific about what it needs to do for you.  AND you need to be comfortable knowing that if you don't get what you want in the time frame you want it, you are ready to move on.  He is still nervous about this, but agreed to have a specific discussion with his manager about a 6 month plan to change his profile to a multi-team leadership role.

I recommended this course of action rather than moving out, because ultimately, management promotions are mostly based on trust, not on competence in management.  Especially the leap from junior to senior or mid-level management.  As a senior leader, I need you to be assertive if I'm going to give you a larger leadership role *and* I need to trust your ethics, orientation and integrity are in line with my expectations.  Using the trust network in his organization - the people who can vouch for him - and being assertive about his needs would be the best way to get that opportunity to show the world what a fantastic leader he can be (and I think he will be).

I hope this was helpful for anyone reading.  I'm taking on clients for executive coaching, organizational development and technical advisory services.

Thanks for reading! Jacob

Jacob Singh
CTO in residence at Sequoia Capital. Independent product and Engineering Coach Mediocre guitarist, singer, rock climber, point guard and baker Dedicated dad. American in New Delhi.
New Delhi