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9 April 2021
The reinvention of working in sales – as explained by Jerry Maguire
Flickr © Susan Murtaugh

The reinvention of working in sales – as explained by Jerry Maguire

Sales, owned for decades by people who are good with people, a job that requires intense networking and face-to-face meetings, is now happening 100% remotely in most countries. From leadership to managing prospects and customers, what are the key learnings of 2020 and best practices to apply in 2021?

Key leaders have been thrown into an unforeseen situation. Sales professionals have had to reinvent how they form relationships and intimacy – much like Jerry Maguire. Once the proverbial king of the world at Sports Management International had to reinvent himself after being fired. So too do the world’s sales departments. 

B2B prospecting has never been more digitally based than in the last 18 months. To address the subject of physical separation and its implications, let’s look into these three categories: the remote leader, remote prospecting, and remote relationship-building, simply because:

 ‘A positive anything is better than a negative nothing.’ – Locker Signs, Jerry Maguire movie

As a leader, how do you keep inspiring and motivating your troops when social interaction is considered essential to wellbeing? Much like you would for your annual sales kick-off meeting, invite external speakers to boost morale. As leaders, you surround yourself with overachievers and successful people. Ask them to join your team meeting and share their experiences. Not only does it symbolise recognition to your peers, but it will also bring new sources of inspiration and energy to your people.

Dorothy Boyd (26-year-old single mum): ‘In this age, optimism like that is a revolutionary act.’

Sales teams often complain they are not listened to.  Encourage your team to share their struggles and objections, work to address these with thorough follow-ups and, most importantly, provide regular updates and progress on this.

Jerry Maguire: ‘I am out here for you. You don’t know what it’s like to be ME out here for YOU. It is an up-at-dawn, pride-swallowing siege that I will never fully tell you about, ok? Help me… help you. Help me, help you.’

How do you avoid falling into the trap of micromanaging and becoming over-demanding on reporting? Routine check-in and mandatory every morning team coffee may have been fun in the first weeks of the COVID situation. In the long run, it defies the purpose of a well-oiled operating rhythm. Favour efficiency over control; avoid scheduling meetings at lunchtime, after 6pm, or at the last minute.

Jerry Maguire: ‘There is such a thing as manners, a way of treating people.’

Maintain key vital meetings such as team gathering, deal reviews, and favour accountability and execution in your communication. Favour short, actionable emails and structured follow-up, avoid the multiplication of avenues (Slack/email/Drive…) in your transmissions.   

Dorothy Boyd: ‘Stop … just stop. You had me at hello.’

How can you keep the most essential element of all with your direct report – trust – intact? Don’t forget that being a manager is also about assisting your people in being the best version of themselves. Do not assume they understand what you are going through. Educate them on the importance of open communication and transparency. Trust goes both ways. As always, a leader should lead by example: create open agendas and don’t be scared to add your personal time, sports, and family lunches in there. 

Jesus of CopyMat: ‘That’s how you become great, man. Hang your balls out there!’

Remember that you used to spend time traveling, talking to your teammates, debriefing after meetings. You might even have gone to lunch. These moments were valuable opportunities to get to know each other and learn how to work more efficiently with one another. Making personal conversation is essential in creating intimacy, whether within the team or with a potential client. 

Transport time used to be a routine part of the salesperson’s day. It was a time for self-reflection, admin catch-up, and email follow-up. With the pandemic and the need to conduct all meetings remotely, productivity has increased drastically. Instead of the traditional two to three sessions, you can now pack your day with up to seven customer interactions. More if you’ve managed to reduce the time of each meeting to 30 minutes. 

But managers still need to fit in casual check-ins and non-business-related talks. Ask about the family, the kids’ school, or share cooking and fitness insights. Productivity is not about working non-stop behind a computer for eight hours. Many studies have proven it’s necessary to recharge through break time for physical activities, lunch with the family, and possibly, personal development.  As a leader, recognising these elements is essential Why not organise a walking outside team meeting?

Jerry Maguire: ‘But if anybody else wants to come with me, this moment will be the ground floor of something real and fun and inspiring and true in this godforsaken business and we will do it together!’

In 2020, some B2B companies saw their sales and pipeline drop. Others boomed. Digital transformation has accelerated everywhere. Prospecting in times like this is a bit of why and a lot of who. Are you targeting the right companies at the right time? Are you mission-critical to the companies you are trying to reach? After all, inside sales and large territory salespeople have been doing it for decades. It is a matter of adjusting. Here are some best practices: 

  • Select prospects to whom you will be a priority (annual report, strategy, press announcement)
  • Select personas and craft personalised messages; use social media to connect with prospects
  • Offer short meeting connections and virtual coffees 

Many sales professionals are currently struggling with creating intimacy and expanding their network. If you have held a Zoom meeting with five people, connect with them individually with a thoughtful message on LinkedIn. Suggest a 15-minute phone call and meet in a more casual environment. If you notice some people are invited to your presentation, do your best to connect with each of them individually and collect their expectations before the general meeting. If someone is copied in an email, understand why by connecting with them. 

Invent new ways of creating expenses. Did you use to take your prospect to lunch? Have a chef’s lunch delivered to their door. Do you live in the same town? Give them an opportunity to go out on a walk combining exercise and safe proximity. Think about sending boxes of refined coffee, tea, or cakes to share and talk about on your virtual catch-up.  Are you planning a virtual event? Why not invite your key prospects with a physical postcard? Be creative!

Jerry Maguire: ‘All right, I’ll tell you why you don’t have your ten million dollars. Right now, you are a paycheck player. You play with your head, not your heart. In your personal life, heart. But when you get on the field it’s all about what you didn’t get. Who’s to blame. Who won through the pass. Who’s got the contract you don’t. Who’s not giving you your love. You know what, that is not what inspires people. That is not what inspires people! Shut up! Play the game, play it from your heart.’

Don’t forget that personal assistants are resourceful and can provide you with critical insights and networking in an account. Talking to one person is not enough. Do not fear asking for a warm introduction. Do not think you are losing time talking to those who are lower down in the org chart. 

Dicky: ‘The key to this business is personal relationships.’ 

Last, but not least, do not forget to look at expanding your knowledge of remote working and networking tools. I have personally discovered recently Klaxoon, Open Broadcaster Project (for the geekiest of us), and mmhmm. Adaptability is the key to success. As new methods start to dominate and doing business remotely becomes more permanent, reinventing how you do it will be essential to both your success and your wellbeing. 

Dicky Fox: ‘Hey, I don’t have all the answers. In life, to be honest, I failed as much as I have succeeded. But I love my wife. I love my life. And I wish you my kind of success.’

Caroline Franczia is a regular columnist for Maddyness, the author of Popcorn for the new CEO and the founder of Uppercut First. Experienced in working for large companies such as Oracle, Computer Associates, and BMC, Caroline also lived in Silicon Valley for four years before moving to startups (Sprinklr, Datadog, Confluent) where she witnessed on the ground the benefits of a well-thought sales strategy. These are the foundations of UF: a structure that accompanies the European startups in their sales strategy by giving them an undeniable advantage in their go-to-market.

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