Hi Krish, I am so sorry for not getting back to this question until now – I hope you can forgive me. I know it’s a slow one, but I really wanted to respond because it’s a great question!
I think we made a lot of mistakes in our early days where we hired people that weren’t more senior than ourselves, and so we all ended up making a lot of mistakes together – it’s never a good situation when you run into problems for the first time yourself, and it’s very refreshing when you have people on the team who have “seen it all before” and can at least offer guidance on how to tackle problems, so you’re not always learning from scratch with every issue that comes up.
I think key to bringing experienced people in is to treat them as such – there’s no point bringing amazing, experienced people in and then to tell them how to do their jobs(!)
So underlying this, for me, it’s really critical to have the “foundations” solid:
- The goals of the company
- At least a short to mid term plan
- The roles and responsibilities and how they break down between everyone – avoid overlap and gaps
- To always assume good intent – it helps when anyone screws up (and we all do)
And in terms of existing team members, it depends on the roles and who is in what position. I think it’s very hard when / if you need to hire someone “above” an existing team member, but hopefully this never comes as a surprise to either party.
Also – if you’re bringing on anyone more experienced – this is almost certainly a step in the right direction, assuming they’ve been hired based on the right decisions and rationale. So everyone on the team should be thrilled – it’s someone to learn from, to gain experiences from.
Somewhat tangential, but I also think there is tremendous value in the early days of any business in naivety – in not knowing everything. That naivety can drive radically different thinking and seemingly crazy bets, and that thinking, and lack of “playing it safe” can be as transformative as it can be dangerous. It’s great if there can be a balance of naivety and experience, and for an appreciation on both sides of what the other brings to the table.