Ask HN: What was the biggest leadership challenge of your career?

Thanks for the long and very helpful reply. I wrote back but it also got really long... -- Yeah we have 2 year cycles so 21 is 'off' 22 is on with some good work actually municipal or ballot measures in 'off.' we typically ramp up 3rd quarter of the odd year. We hired a new senior manager/client connector role early 19 and brought on the handful of new FTEs last half of 19. This year feels slow, not having census & new districts I think is hard.

YES. That's the exact same struggle we have! making that transition from partner lead, partners doing the work, to having a more distributed 'assembly line' delegation of work to more employees.

that's good advice on client expectations. It's a struggle politics is crazy - very hard to explain just how crazy until you've worked there which is a problem unto itself. democrats really lack technical skill (at the level HN knows) because even most startups don't seem as chaotic and they pay way better. candidates themselves at the Congressional level can be the worst in causing this crazyness.

another good frame that you mentioned is thinking more in an engineering mindset of systems design might help me thank you! micro-services haha.

UGH yes pricing is the worst. That lower margin, higher volume growth is what we're trying, but I'm not sure it might be better to stay small with higher profit margin. We made slightly less profit this cycle despite having over 2x the retainers. I'm money driven so always want more so it's a big decision for us. We're going to try again this cycle - it's not like I'm struggling here, I still am doing well!

Sounds like your experience is similar on pricing. there are so many people who want to do good, come in and start a digital agency and charge no joke $2k or $3k a month for a LOT of work. And candidates and campaigns are super super cheap but in a really dumb way. Especially Democrats. Republicans will pay a flat % of what you raise, in that case the free market really does work - though sometimes too much bad incentive lots of gross (fraudulent) tactics; read the recent Trump/RNC pieces on their fundraising pages.

An example differentiator that is hard to sell or explain is we use an ESP that I don't think any other political shop use because the political features / tooling doesn't exist. I built that on top to make it fit political needs - and some other cool things like real time data for wayyy quicker reporting. I see the value, clients usually don't but most still trust us.

That switch alone usually gives a 4+% open rate bump which usually equals more than the difference in cost.

We tend to fit best & win more work with clients where there is an existing human relationship of good work or from the parent committees where our work and reputation is good, rather than just cold pitching on price to someone we don't know - much harder to win an account cold.

One good sign that we're doing some things right I actually just saw a report comparing digital firms congressional ad revenue and was surprised to see much bigger companies didn't actually have much higher Congressional ad revenue than us. But those big guys have bigger non-profit clients.

So that's a key goal for us to get more advertising. which in itself is hard; TV firms fight to keep their 'primary general consultant' monopoly even if they have no digital experience. It's gross we sometimes have to do commission splits have to give a % to tv firms just to do the digital buying (they don't do anything we do the work.. they say it's because they made the TV spot, but after charging the campaign $40k in production you'd think the campaign owns it...) sucks. but tv guys are the top historically that's who steers the ship right or wrong.

Plus Democrats barely spends on digital. It's ridiculous like PG, Coke whoever gets it and follows eyeballs and $ quickly. Dems are SO far behind despite seeing campaigns that spend more on digital ads tend to win more!

And again thanks for your input and just sharing your story, it helps I think just to connect and know we're not alone.

"Company > Team > Self in terms of goals, if I cannot accept that, I'll move on to a different gig." - This is a great lesson, however I would add Customer at the very top as that is whom the company exists to serve. Customer > Company > Team > Self. So many people I have seen who put themselves (I've been guilty of that myself) before Team or Company and then it leads to stress and work suffers.

Agreed. For a customer centric company, it's definitely true (although some companies are not like that, and sometimes thrive anyway).

It's a prejudice about the human doing the work. It's not complicated to understand what the problem is. You should judge the work on the intrinsic merits of the work, not the worker. Every human has the right to work and be evaluated on the work, independent of the nature of their birth.

> In many countries it wouldn't have been allowed to fire him.

I'm in one of these countries. If they have a cause that cannot be legally used to terminate an employee, they just look long and hard for any other misdemeanors and fire them as fast as they gather any plausible "evidence". Creative types can also actively put an employee into a checkmate, i.e. a position where no move or any move is a fireable offense.

In this case it could be as simple as identifying any part of that email as a defamation.