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How to Use One-on-Ones to Supercharge Your Sales Career

How did your last one-on-one go with your manager? Did you walk away with new information and a plan to improve your work? Or did you spend most of your meetings going through a checklist of sales tasks?

If you want to supercharge your sales career, take the reins in your weekly one-on-one meetings. You’ll get the most value out of your time when you show up with an agenda, a plan, and a bit of empathy for your manager as well.

If you don’t already have these meetings scheduled, you’re missing out on the support and guidance you need to reach your goals. When teams have weekly or biweekly one-on-ones to discuss goals, their confidence in reaching those goals increases by 2.7x.

If your one-on-ones need some work, read on to learn what subjects to talk about in your meetings and the best practices to follow in order to get the most out of your time with your manager. Plus, we added some bonus questions to help you get started.

Your chance to build trust with your manager

If your one-on-one meetings tend to focus on status checks for each individual sales deal, you’re doing it wrong. Luckily, you can take charge of your meetings by setting the agenda in advance – and make your manager’s life easier at the same time.

Your one-on-one meetings are the perfect time to discuss how you can improve your work, what you need to do to achieve your career goals and to understand the broader team and company objectives.

Make sure you’re meetings include:

  • Allocated time for your manager to give you guidance on job priorities and goals
  • Opportunities for feedback on how to improve your day to day work
  • Chances to request coaching or seek advice on upskilling
  • Opportunities to connect with your manager personally and understand their goals
  • Time to discuss your career plans and growth opportunities
  • Opportunities to understand how your work is connected to business goals

Far from being upset that you’ve taken over the agenda, your manager will actually appreciate how you’ve given them time back. Running one-on-ones with every direct report takes planning and time and your proactiveness adds a lot of value to their day. Building rapport with management is also a good first step towards reaching your next promotion.

One-on-one themes and discussion topics

You can’t cover every important topic in each weekly meeting. There just aren’t enough minutes in the day. Plan to cover discussions about career planning and self-improvement at least once a month. Topics like your day-to-day needs, personal updates, and how you can help your manager should be talked through weekly.

Your sales activities, targets, and roadblocks

When your manager wants to discuss your open opportunities, don’t show up with a messy forecast. Be prepared with up-to-date data. This way, your manager knows what they can do to help you now, like talking to other team leads, asking for flexibility from the finance department, or giving you guidance on next steps.

Anything urgent should be discussed at the beginning of your meeting. For example, if you know you're going to fall short of your target this quarter and need to find more opportunities fast, your manager can help you review customers, closed-lost opportunities, and leads for low-hanging fruit.

Self-improvement and upskilling

No one can do their job perfectly and we all have areas that we can improve. Sometimes we know what those issues are and sometimes we don’t. Your manager will have insight here. For example, if you’re struggling to work with another team, ask your manager what you’re missing. They can usually give you insight into how that team is measured, their workload, and how to communicate your needs better.

Career goals and professional development

It’s great when a manager is proactive with their direct reports about career planning. Most managers want to help their employees achieve their dreams, but unfortunately, they’re usually focused on more urgent concerns.

If you want to discuss your career, give your manager a heads up and put it on the agenda for your next one-on-one. Ask them what you’re doing well and what you need to improve to secure a promotion.

If you are interested in moving to a different team or department eventually, your manager probably knows who to introduce you to for a chat. They also might know what roles will be opening up soon.

Help a manager out

Sellers are expert jugglers and can keep a dozen priorities moving at the same time – but it’s always nice to have some help. Your manager is in the same boat with goals they would love to work on but just don't have enough time. Ask your manager how you can help them this month with tasks like setting up team meetings, pulling sales reports, and mentoring new hires.

Personal updates

If you’re struggling to get your work done because of personal issues outside of work, tell your manager about it sooner rather than later. They’ll help you offload some work, push out deadlines, or take over a few tasks that need to be done urgently. Illness, family issues, financial problems, childcare problems, and your personal safety are all important to your manager.

Role and company goal alignment

Everyone is working towards a larger company goal. It helps to understand how your work is connected to this success. Find out how hitting your sales target will help your company innovate so you can connect with the real purpose of your work.

Your organization may be planning to fund and build new products, strategically acquire another company, or ensure that investors are happy before a new series of funding. You’re not just throwing your work into the void, you’re helping your team reach bigger goals.

Best practices for effective one-on-ones

  • Show up prepared. If you’re forecasting with your manager and you haven’t cleaned up your sales data, you’re wasting both of your time.
  • Don’t work on other tasks during your meeting. Close your email and messaging app. Put your phone away. Be present in the meeting and give your manager your full attention.
  • Create an agenda in advance for each meeting. When writing down what you want to cover, leave enough time for each topic. You can’t talk about everything that’s important, so spread out topics over the course of a month.
  • Ask your manager questions. Otherwise, you’ll feel like you're being grilled on what’s most top of mind for them at the moment. Neither of you wants to make your meetings all about crossing things off a checklist.
  • When you receive feedback on how you can improve, create an action plan with next steps and a deadline or check-in date. Perhaps you need to improve your communication skills and plan to report your progress in one month.
  • After the meeting, send an email that lists out what you talked about, what you need to do, and the tasks that your manager also agreed to.
  • It’s discouraging for a manager to have the same conversation every one-on-one meeting. If you asked them for career advice and they gave you steps to take, make sure you act in a reasonable amount of time. If you don’t prioritize it, you’re telling them that either you didn’t really care about that subject in the first place, or you don’t value their help and guidance.
  • If your manager asks to cancel your meeting for this week because of other obligations, request to reschedule it instead. Otherwise, weeks can go by and you won’t have any dedicated one-on-one time with your manager.

13 questions to get you started

To get the ball rolling, here are our top questions you should bring to your one-on-one meetings.

  1. What am I doing well? Can you give me feedback on what you’re seeing?
  2. Are there any processes or approaches I can change or improve?
  3. Is there anything that I’m doing that I should stop doing?
  4. In your experience, what is the typical timeline for a promotion in my career path?
  5. What skills does the company need to see for my promotion?
  6. I’m open to different career paths, is there a role you think I might be a fit for?
  7. How can I help you and the team this month?
  8. A few teammates have asked for my advice on a topic. Can I host a training session in our next team meeting?
  9. Can you point me in the right direction for learning and development courses?
  10. In your opinion, what do you see as my blind spots?
  11. Are there certain tasks that I can take over for you this quarter?
  12. I know what role I want next, can you introduce me to the right person to discuss what they’re looking for in a candidate?
  13. I repeatedly have issues with a certain process, team, or person, can you help mediate these conversations?

Take the lead in your one-on-ones

These meetings are for your benefit. If you come prepared with up-to-date data, a clear agenda, and ways to help your manager and your team, you’ll see a smoother trajectory in your career growth. By becoming a trusted and reliable partner for your manager, they’ll be more than happy to help you along the way.

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