10 Rookies Mistake You Must Avoid In 2026 | Donald C. Kelly - 1969

We’re a month into 2026, so there’s no time for rookie mistakes. In this episode, I’m breaking down 10 common mistakes sellers make and how to avoid them. Catching these early can help you set yourself up for success for the rest of the year.

1. Not Having Enough Deals in the Pipeline

• One of the biggest mistakes I see is not having enough opportunities in the pipeline. I recommend carrying three to five times your quota in active deals to protect yourself when prospects go quiet or deals fall apart.
• When you consistently add new opportunities, your sales engine keeps moving even when the market shifts.

2. Not Using LinkedIn Effectively

• Too many sellers are underutilizing LinkedIn as a prospecting and research tool. I encourage upgrading to Sales Navigator, multi-threading within accounts, and posting consistently.
• Staying visible helps you build familiarity and turn cold outreach into warmer conversations.

3. Waiting Too Long to Involve Stakeholders

• Relying on a single champion is risky. Most B2B deals involve multiple decision-makers, so it’s important to identify and engage stakeholders early.
• LinkedIn is a great way to map the organization and start those conversations sooner.

4. Skipping Daily Prospecting

• Pipeline growth does not happen by accident. Prospecting needs to be a daily habit.
• Blocking time each day and testing different outreach windows helps create consistency and avoids feast-or-famine cycles.

5. Lack of Planning and KPI Tracking

• Planning your week and your day is non-negotiable. I recommend blocking time for prospecting and meetings, then tracking KPIs like calls, conversations, appointments, and closed deals.
• Reviewing these metrics helps you see what is working and where you need to improve.

6. Ignoring AI Tools

• AI is changing the way we sell. Tools for note-taking, research, and CRM updates can save time and reduce admin work. Testing AI solutions now helps you stay competitive.

7. Not Asking for the Next Appointment

• Every meeting should end with a clear next step. I always leave a few minutes to schedule the follow-up so momentum does not stall.

8. Missing Red Flags

• Hesitation around pricing or commitment should not be ignored. Address concerns early by asking direct questions before deals slow down.

9. Not Going Deep Enough on Objections

• Surface objections are rarely the real issue. Dig deeper to uncover what is truly holding the buyer back.

10. Selling to the Wrong Pain Point

• Before pitching a solution, make sure you understand the prospect’s real problem. When the pain is clear and validated, demos and proposals land much more effectively.

“Don’t sell to the wrong objection or try to solve the wrong problem. Commit to going deeper, uncover the real reason behind the objection, and address that directly. That is your job, and it’s one of the most important things you do in sales.” - Donald Kelly

Resources

Sign up for free and download the Sales Evangelist Tracker to monitor your sales KPIs, measure performance, and stay accountable to your daily activity.

Join the LinkedIn Prospecting Course to improve how you use LinkedIn and book more consistent, high-quality sales appointments.

Visit Blue Mango Studios for help in creating podcast production content.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.