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Leadership in Tough Times

February 13, 2014 by Ben Yoskovitz

captain-america

The all-time most popular post on this blog is 10 Essential Business Leadership Skills. I wrote that in 2007. It ranks near the top of Google results for “leadership skills” (which is what drives most of the traffic).

I’ve struggled from time-to-time since then with my own leadership abilities. Writing ideas down about how to improve as a leader is one thing, actually living it daily is another thing entirely.

One of the biggest challenges with leadership is what you do when times are tough.

When things are going well, it’s pretty easy being a leader. The good stuff drives a lot of the motivation, and you just need to keep people on track and serve, in many ways, as a constant cheerleader and supporter of everyone’s work.

When things aren’t going well, a lot of people retreat into themselves and don’t tackle the problems head on. They communicate less. They get paralyzed. They react negatively to feedback and try willing things into existence (which doesn’t work) as opposed to taking a proactive approach to solving problems. I’ve done all of those things.

I’d like to think I’m getting better at leading through tough times, but for most of us, it’s not natural.

Here’s what I would challenge you to do when things aren’t going well: communicate more. Invest more time in communicating with team members on what’s going on, be honest and straight. Don’t sugarcoat. On the flip side, keep your emotions in check and don’t make a bad situation worse. Most likely the sky isn’t falling. The world isn’t ending. You have to remain calm. Just tell it like it is.

I would challenge you to communicate more with employees, but also with your investors. I know that admitting “weakness” to investors, or that you’re facing challenges is scary, but once you stop communicating you lose investors’ trust and they write you off. Fast. So during the rocky parts of your business (and there will be rocky parts), communicate more.

I used to yell a lot more than I do now. These days I still display frustration, but less so, and I try very hard to remain action and results-oriented versus blustering and grumpy. What might come off as grumpiness is really just me being focused. But there’s a delicate balance there. Leaders have to be passionate–if you don’t care, why should anyone else? But there’s a fine line between passion and panic. Be careful about crossing that too often.

When the shit hits the fan, lead by example. Communicate actively. Direct people clearly. Stay calm. Be action and results oriented. Get problems fixed as fast as you can. Go for small wins to re-energize everyone. Remain until the end. Don’t spend time reflecting on what happened, do that later. Don’t play the blame game; decompress after.

In some cases, when times are tough, there’s no immediate answer. At some point as an entrepreneur / leader you won’t have the answer. (It happens to me all the time!) There’s no quick fix solution. It’s in those times that you can be a great leader or turtle and give up. It’s in those moments when you can open up, admit that you don’t have the answers and get everyone around you helping. Your employees and your investors are working with you because of you–that’s a huge burden but also a huge opportunity to leverage the resources around you for help. Don’t close yourself off to that. People will rally around you, and that’s a way better feeling than sitting in a dark room alone trying to solve all the problems yourself or praying for a miracle.

Photo courtesy of stickkim.

Filed Under: Entrepreneurship

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Ben Yoskovitz

Founding Partner at Highline Beta, a hybrid venture studio and VC firm that works with large, ambitious companies to identify new areas of opportunity through internal and external innovation.

Previously I was VP Product at VarageSale and GoInstant (acq. $CRM), and Founding Partner at Year One Labs.

Angel investments include: Breather, Spoiler Alert, SendWithUs and others.

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