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Tips for Sales Leaders to Survive and Thrive

Repeat after me: I will not miss another ski trip. Or holiday dinner. Or football game. Or high-school musical. Now say it again, but this time with feeling.

I’ve led more than my share of sales organizations, and I know what it’s like to feel as though Q4 is actually killing me — or at least beating me to a pulp.

It’s the last chance to make your numbers, plus you’re working on planning for next year — building out a strategy, determining a budget, creating organizational and compensation models. Then there’s preparation for sales kickoff, which starts at what seems like 12:01 am on Jan. 1. And I haven’t even mentioned spending holiday time with friends and family and even colleagues, or all the other distractions that come with “the most wonderful time of the year.” The competing priorities seem as though they are conspiring to defeat you at every turn.

I’ve been doing this long enough to know there are tangible things you can do to make sure this time, this year, is different. I know you’re thinking that ship has sailed, since Q4 is, like, tomorrow, but I am here to tell you it’s not too late. Follow these tips to survive — and maybe even thrive through Q4 and into the new year.

Prioritize your time, and make a map.

Prioritizing sounds so much simpler than it actually is, but you really need a detailed plan for where you’re going to spend time through this quarter. Take a minute to figure out where your remaining selling days are, and consider the length of your sales cycle. Know when your customers are available (they have competing priorities and time OOO, too). When are your budgets due? When can you start any hiring you need to do? And, of course, when is your big family holiday hooha? BOOK IT into your calendar, and don’t miss it. I make a map of everything using both paper and technology, so it’s always staring at me, to ensure everything gets done.

Let someone else be the hero.

Sales leaders — all salespeople, really — love the win. They love to be the deal closer. They love to make things happen. But when you’re a sales leader, you’ve got to depend on other people to do that. You just can’t be the hero on every deal, and you need to make peace with it, because you have other things to do. Make sure your folks are executing appropriately, and definitely stay on top of deals, but you don’t have to fly to every deal to be the closing hero. I’ve seen it so many times: A sales manager flies in at the end to have a 15-minute conversation their rep could have easily had. Don’t do it. You don’t need the credit; you need the time.

Delegate, delegate, delegate.

Deciding how and what to delegate is a matter of truly understanding your team and their specific strengths, then combining that knowledge with the criticality of the task. If my No. 1 issue is that I’ve got to stop and figure out what next year is going to look like and how I’m going to hit my budget, and I’ve got a couple of great sales reps I can trust to get deals done — but no one who excels at working on forecasts — I work on the forecast. Delegate to the strengths of your team. If you find you have no one to delegate to, well, you’ve got some development work to do with your team next year. In the meantime, see No. 5, below.

Align your resources.

Oftentimes, you need different resources from across your organization to close business. For example, maybe you need somebody to talk to a potential customer at a more technical level about the product. Chances are they don’t report to you, so you need to understand your extended team’s availability. Work with your peers to ensure those resources are deployed in a way that supports the whole business. If your peers are in their own Q4 hell and say they can’t help, well, that’s a conversation you’ll need to take to the executive team about where the company most needs those resources. Sure, it’s a whole lot better if you can work it out at the peer level, but don’t be afraid to bump it up the chain in Q4 — if you don’t make your numbers, you’re the one on the hook.

Hire reinforcements.

If you’re having trouble executing or delegating, a temporary shadow or consulting sales leader can be exactly what you need. First, figure out where your bottlenecks are. For example, if you’re spending a ton of time just doing reporting for regular meetings, think about bringing in a sales ops consultant for some period of time. They can also help you implement your sales model and strategy for next year. Once you know where your holes are, plug them with outside talent.

Analyze your Pipeline

Know where you stand with every deal. See which ones you believe you’re going to get, as well as which deals are iffy but a good fit and a significant size. Which deals are just not even a fit with your market? Understand those things and their impacts. If you close all the deals you know you’re going to get, will you make your numbers? That’s something most sales leaders have running in their head all the time, but formalizing it can give you a great picture of where to marshal your resources. And if you realize you don’t have enough pipeline, identify new opportunities, and expand your pipeline as early in the quarter as possible (like now).

As if there weren’t already enough swirling around in your brain, there’s something else we have to think hard about this year: the uncertain economic climate. Are we going to grow? Are we going to sink into a recession? You read an article saying one thing one day and another one the next day saying the opposite. It’s an unknown, so you need to be prepared. This year, modeling most likely as well as  best- and worst-case scenarios — and accompanying “what if?” plans — is more important than ever.

Stay on top of your sales process.

If you start getting busy and ignore the basics, such as weekly one-on-ones, analyzing your pipeline and making sure your sales process is being followed appropriately, there’s a greater risk deals are going to slip into Q1. Keep focused on your process, and work it.

Encourage downtime.

If you’re following my advice and not killing yourself in Q4, please also check on your team. Are they running themselves ragged trying to balance the requirements of work with the obligations of the season? Don’t underestimate the value of downtime, even if it’s forced, even if it’s short. Manage your own stress level — I fall back on taking my morning hike and drinking a ton of water — to ensure you can be as effective as possible, and encourage your team to do the same.

To quote JFK, “Things don’t happen, they are made to happen.” OK, he wasn’t a sales leader, but the words ring really true to me. A great Q4 isn’t just going to happen — and a great Q4 shouldn’t be defined solely by your numbers. At the end of the day, we need to hit the numbers, but you don’t need to sacrifice your life to make that happen. If you take my suggested steps to heart, on the eve of Q1, you should be having dinner with your family or skiing wherever you love to ski, all the while knowing you’ve made your numbers and you’ve survived — maybe even thrived — through another Q4.

 

 

Lindsey Anderson

Lindsey Anderson is Managing Partner of CROs2GO, a division of 2GO Advisory Group. Lindsey has more than 30 years of experience in revenue leadership roles, primarily in technology, including software, SaaS, and hardware. In both CRO and VP Sales (and Marketing) experience with Seed, Series A and B startups, mid-size companies and global public companies.

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