When to walk away from a deal (and when to push harder)

Every salesperson has faced this dilemma: Do I push harder to close this deal, or is it time to walk away?

The best sales professionals know that not every deal is worth fighting for. Chasing the wrong prospects wastes valuable time, energy, and resources; time that could be spent closing deals with qualified buyers who truly need your solution. On the other hand, some deals require persistence, strategic negotiation, and a little extra pressure to get over the line.

So, how do you know when to push harder and when to let go?

Signs you should walk away: 

1. The Buyer Isn’t Serious

If a prospective buyer constantly delays, reschedules meetings, or keeps saying they’re "thinking about it" without moving forward, they may not be a serious buyer. The modern day “continuous ghosting” is also a sign you may need to walk away. The issue being: if you can’t speak to them, how can you possibly influence them? 

Red flag: They avoid discussing budget or decision-making authority. Avoiding you entirely.
Walk away if: They won’t commit to clear next steps or deadlines.

2. The deal will be a loss (or barely profitable)

Some deals look great on paper but end up costing you too much time, effort, or margin. Deep discounts, excessive demands, or a low-value contract may mean the deal isn’t worth pursuing. Beware of clients who will only go ahead with you if you “cut them a deal”... they will likely want a deal from you forever so you’ll always struggle with your long term GP%. 

Red flag: They demand unreasonable pricing, unlimited support, or custom solutions that don’t fit your offering.
Walk away if: The effort to close and delivery on the deal outweighs its profitability… no matter how desperate you are to hit target for this month! 

3. The prospect isn’t the decision-maker, and they keep claiming they are

You can have the best pitch in the world, but if you’re talking to someone without decision-making power, you’re wasting your time. Time and again we coach salespeople who tell us that their main contact claims to be the actual decision maker when they simply are not. We give them many tips on how to get the influencer to either introduce you to the decision maker or how to train the influencer to pitch for you to the decision maker. 

Red flag: They say, “I’ll need to check with my boss,” but won’t introduce you to them or tell you anything about their boss.
Walk away if: You can’t get access to the real decision-makers after multiple attempts… or aren’t able to “coach” your contact to selling for you. 

4. The client isn’t the right “fit” 

Not all clients are a good match. If a prospect disrespects your time, is rude, or has a reputation for being a difficult client, it may be best to step away. You may have a clash of values, personality or even culture. That doesn’t make them, or you, a bad person, it simply means there isn’t a long term fit. 

This is critical: over 95% of businesses want long term, profitable, clients. They even rely on word of mouth referrals from their existing clients, in order to grow. As a result, you want to only win clients that you and your operations team will be happy to serve long term… especially because painful clients often hang out with other painful clients! 

Red flag: They undervalue your expertise, try to exploit your time, or treat you and your team disrespectfully.
Walk away if: The client’s values, work style, or ethics don’t align with your business… especially view this with a long-term perspective. 

5. The Sales Cycle has No End in Sight

Long sales cycles are normal for some industries, but if a deal drags on with no real progress, it’s time to reconsider. While most B2B sales now happen at the 8th point of contact or later, you have to be careful not to remain open-minded forever: your job is to close sales. 

Red flag: Months of back-and-forth with little movement toward closing… such as a client never explaining how they will actively pay for your solution.
Walk away if: They keep postponing a decision with no clear timeline.

When to push harder:

1. The prospect has a real need, but is very hesitant

Sometimes, buyers know they need your solution but struggle to make a decision. If their hesitation comes from fear of change, uncertainty, or budget concerns, pushing a little harder can help them take action.

Push harder if: They acknowledge the problem but hesitate on the next step.
How? Reinforce your ROI, reduce risk by sharing case studies, and let them call a referee who will give you a glowing reference. Another tip: ask them “what’s the worst that can happen if you DO go ahead?”, then “what’s the worst that can happen if you DON’T go ahead?”

2. There’s strong interest, but internal barriers exist

Some buyers face internal challenges, budget approvals, competing priorities, or risk-averse leadership. If the prospect is engaged but stuck in bureaucracy, persistence can make a difference.

Push harder if: They are excited about your solution but dealing with internal red tape.
How? Offer to help them build a business case or speak with other decision-makers. This is a HUGELY valuable technique used by fewer than 20% of salespeople. Getting great at coaching clients through making internal businesses cases is very valuable. 

3. They keep comparing you to a competitor

Many prospects get stuck in a decision paralysis between you and a competitor. If they’re still talking to you, it means they’re interested, they often just need reassurance to change.

Push harder if: They’re evaluating you against another option but haven’t ruled you out.
How? Highlight your unique differentiators and even offer a trial, if appropriate. Be sure to maximise your fact finding also: find out what they do like about the competitor and find out what they wish the competitor did that they don’t! 

4. They have a fast-approaching deadline 

If a prospect has a real pain point and a looming deadline, a little pressure can help them stop stalling and make a commitment. You see, sales is often a “pressure” game: the closer to a deadline someone gets, the more pressure they feel, the less negotiating power they have, the more likely they’ll be to accept an agreement. 

Push harder if: They need a solution soon but haven’t taken the final step.
How? Use urgency-based messaging like limited-time discounts, fast-track onboarding or remind them that not making a decision is likely more costly to them than actually making a wrong decision.

5. They’ve invested plenty of time in the process

If a buyer has gone through multiple meetings, demos, and discussions, they are already invested in the process. Walking away too soon could mean losing a deal that was close to closing. They may even come under pressure from their colleagues if they’ve wasted everyone’s time. That’s an advantage for you. 

Push harder if: They’ve spent significant time engaging with you and your team.
How? Remind them of their progress and what’s at stake if they delay further.

Great salespeople don’t waste time on dead-end deals, but they also know when to push for a close. The key is reading the situation carefully; recognising when a deal is salvageable and when it’s simply not worth the effort. Over time, 95% of salespeople gain that “sales wisdom”. 

By focusing on serious buyers, profitable deals, and high-potential opportunities, you’ll close more sales without chasing the wrong prospects.

So next time you’re in a tough negotiation, ask yourself: Is this a deal worth fighting for, or is it time to walk away? Your long term success depends on knowing the difference.

Take your sales team to the next level: complete the Sales Power Score on behalf of your business: https://www.salesmasterycompany.com/sales-ps