The Hardest Part of a Salesperson’s Day (and How to Move Past It)

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Dan Tyre
Dan Tyre


The hardest part of working in sales? So much of it’s in your head. I learned early on that focusing too much on individual customer responses or rejections could be the kiss of death for any sales career.

Even now, I have to remind myself sometimes the sales process is a marathon not a sprint. One sale doesn’t make a week, one week doesn’t make a month, and one month doesn’t make a year. It’s important to find the right balance between bringing a healthy curiosity to each meeting and connection and knowing statistically some calls just won’t go your way -- and that’s alright.

I asked a few of my HubSpot Sales colleagues what the hardest part of their day is and how they overcome it. I’m sharing their responses below, along with some additional tips on how to overcome hard days, bad calls, and an overwhelming workload.

What’s the Hardest Part of a Salesperson’s Day?

When everything feels like the highest priority

Flora Wang, a sales engineer at HubSpot’s Cambridge office says, “The hardest part is prioritizing which tasks to tackle. Sometimes it feels like everything is the highest priority and you have to make a choice and balance mindfulness for yourself.” Flora’s absolutely right. When I’m building my to-do list for the day, I make it a rule only to have three high-priority tasks -- and sometimes even that is too many. If I try to tackle more than three priorities in a day, they all begin to blur in frustration.

You have to be absolutely vicious with your priorities. Just because something is important doesn’t mean it has to be done today. Decide what’s going to have the biggest impact on your overall goals and go do that.

Flora says, “I schedule specific times to focus on daily tasks.” That’s crucial. I’m a firm believer in having one calendar where you track all your tasks, meetings, and outreach. Take five minutes in the morning to identify what must be finished by end of day, and check back to review if and how you achieved it.

Feeling suffocated by a lack of opportunities.

“Regardless of where I am in the month or quarter, I want to overachieve,” say Senior Inbound Growth Specialist Brendan McCarthy, “and having a full pipeline is a key starting point. We’ve all had that feeling of being suffocated by a lack of opportunities.”

To combat this, Brendan blocks off parts of his calendar every day for prospecting. He says no to meetings, doesn’t work on existing opportunities, and avoids chatting with colleagues. “Discipline is the most important part of this process, and it creates more freedom for me to control the rest of my sales process.”

Brendan’s doing it right. Spending time on outreach and maintaining a full pipeline is the least popular part of sales because it’s so hard. You might leave 25 voicemails and hear nothing back. Generating a full pipeline means more proactive outreach, because the more people you connect with, the better your chances of getting one of them to close.

It’s easy to start questioning yourself and your approach after the 19th unanswered call, which can leave you caught off guard and off your game when someone does pick up. When this happens, remember to be human and humorous.

Customers today have so many choices, it’s impossible -- or implausible -- that being pushy is going to earn their business. Instead, let them know they’re in control by saying, “It’s totally up to you [prospect name]. If now isn’t the right time, I want you to feel empowered to tell me that.” You’ll set yourself apart from the pack, and they’ll never know you’ve just spent the morning sending voicemails into the abyss.

The hardest part of my day is time management

Sandra Wergen is a senior channel account executive in our Germany office. She says, “The hardest part of my day as a salesperson is time management.” She moves past it by “using HubSpot’s Sales Pro tool and blocking out time to focus on certain tasks like prospecting, answering emails, and making calls.”

Sandra’s spot on in her approach to time management. I’d take it one step further and consider the timing of when each task is scheduled. For example, I schedule activities requiring the most thought early in the morning when I’m fresh, and I save administrative tasks like expense reports for later in the day when I’m fried.

I also schedule meetings in 15-minute increments. Not everyone can or should do this, but HubSpot’s Meetings tool makes it possible for prospects and coworkers to book 15-minute meetings. This allows me to be available for quick prospect check-ins or questions, and it pushes us to get right to the point -- which saves everyone time.

When my competitor misleads prospects about our product.

HubSpot Inbound Marketing Specialist Daniel McGreevy is feeling that pressure of competitive deals. He says, “It’s tough when I am in a competitive deal and learn a competitor has mislead the prospect about our products.”

I approach every deal like it’s competitive, and when I’m confronted with misinformation about our product I say, “I’m not sure that’s current information” or “That’s not what my competitive intelligence says.” The best way to build trust with someone is to have a third party weigh in and share their experience, so I’ll usually put prospects in touch with a client who can offer advice or clarity on using our product.

Daniel is approaching his competitive deals in a similar way. He says, “When I’m working on a competitive deal, I always ask if the prospect has any questions or concerns about our value or functionality so I can give them accurate answers.”

However you approach competitive deals, make sure you’re on the same page as your prospect, and always clear the air in a way that doesn’t point fingers.

Recovering from calls that don’t go my way.

Jordan Benjamin is a principal agency consultant for HubSpot Cambridge and struggles with something most salespeople have grappled with at some point: “The hardest part of my day is recovering from calls that don’t go my way.”

It’s statistically inevitable you’ll have a series of calls that don’t go well. This used to really piss me off. Luckily, Jordan and I deal with rejection calls in a similar way. He says, “I bounce back by changing my physical state. I do a few jumping jacks or walk outside to get my heart rate up so I’ll be fresh for my next call.”

I used to get up and walk around the building three times. This wasn’t that unusual during summer, but it got me a few confused glances when I’d do it in the middle of a fierce Boston winter.

I also turn to music. After a string of rough calls, I’ll blare some Def Leppard or Aerosmith to feel better about my day. Finally, I have two or three people I call when I really need encouragement. They know what I need to hear: “Dan, you’re a great salesperson and an even better human being.” Every salesperson should have a few lifelines to call when they need it most.

Something I would remind all salespeople, including Jordan, is that in sales, sometimes you eat the big dog and sometimes the big dog eats you. You can allow yourself to wallow in self-pity for about a day, then you have to move on. Because if you can’t move on from a string of bad calls it might be time to move on to a new career.

I’m also a big believer in video outreach, and I think it’s going to be huge in 2018. I’ve coached a few salespeople on this, and they’ve seen upward of 50% connect when they use video in at least one segment of their outreach.

Keeping myself accountable to completing certain tasks during a certain timeframe.

Tasks with no deadline are sometimes the most difficult to complete in a timely manner. Allison Conroy, an inbound growth specialist with HubSpot Cambridge, sets “an alarm on my phone to force myself to get through my to-do list.”

I’d grab a buddy to help hold you accountable. It’s like going to the gym -- you’re more likely to do it when you have someone to go with. Human nature is such that group activities are more likely to be completed than individual ones. Ask your buddy to check in with you at the end of the day to see how it went, or schedule a few touch bases throughout the day.

There are many difficult parts that comprise a salesperson’s day. I wish I could tell you they go away once you’ve been in the game for a while, but I can’t because they don’t. What can change is your ability to cope with rejection, shifting deadlines, and prioritization. That’s the secret sauce of a long and fulfilling career in sales. Are you ready to do the work?

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