Ask HN: What was the biggest leadership challenge of your career?
My career is young. I&#x27;m only (just about) 32 but own a small agency with a partner.<p>This election cycle was tough.<p>We tried to grow in 2019 with more staff than we&#x27;d ever had.<p>We&#x27;ve always had a leadership problem of trying to transfer skills from the top down to help lift up employees that don&#x27;t already &#x27;have it&#x27; - especially (braggart time) me and my partners skills as I think our uniqueness as a firm is tied to my work in particular (which my parter is very good at picking up) especially tech &amp; a certain unique vertical of advertising.<p>It&#x27;s hard to find employees with multi-skillsets and experience to run things themselves using our tools. especially in politics not a lot of people come in from the outside, and there is low tech skill from the inside.<p>With larger staff we tried to do more training, tried to build stronger team mindset.<p>That I think that&#x27;s our biggest weakness and leadership challenge. Still is.<p>An example from this cycle of it not going well:<p>A big problem is mistakes. Our work is hard, long hours, stressful clients making last minute decisions.<p>One staff member in particular made a large amount of mistakes - and big ones. More importantly didn&#x27;t seem to learn from them. Lost us important clients and reputation.<p>So come end of cycle we usually have to downsize payroll.<p>Choosing who is tough. This year had to decide do we prioritize team cohesion and moral at the cost of mistakes (and our reputation is a big potential issue)? Or do we try to go with more skilled employees who are also more likely to leave, especially without the larger team bonding. Or i guess third option do we take a larger risk than usual in having larger cash loss during down period.<p>We went with higher skill. Well I think it just bit us, losing a key employee to another agency - the same agency the mistake employee landed at. It&#x27;s not a coincidence. though to be fair in our business we usually lose people after 2&#x2F;3 years anyways so maybe just stings more than a disaster of decisions.<p>Hiring is also a leadership challenge for everyone it seems. It&#x27;s almost random given the few we hire which all look promising which ones end up excelling.<p>We need to improve learning skills to be more bottom up if we want to grow. But another leadership challenge: I&#x27;m also not sure it&#x27;s our best path forward. we might be more profitable and successful staying smaller and being top heavy.