Early wins and red flags: Is your start-up on track or off-course?

It’s May. Blink and you’re almost halfway through the year. How’s it looking? Are you cruising along the green line of your plan, or already veering into the red? I talk in my video on the homepage about the importance of monitoring your development and making sure you work hard to stay close to that green line of success – because you’re never closer to it than you are right now. If you’re seeing a divergence, prompt action is ALWAYS the solution, rather than waiting to see what happens. The difference between those two lines can make or break your year.

If you’re seeing early wins, congratulations – but don’t pop the champagne just yet. Early success can be a blip or a trend. And if you’re seeing early red flags – especially lagging sales – don’t despair. May is a powerful intervention point. There’s still time to course-correct and haul your trajectory back to that green line. Leave it until Q3, though, and you might spend Q4 praying for a Christmas miracle. So, what are the early indicators of success in a start-up? And what should you do if you’re already off-track?

Early signs you’re on the right path (green line signals)

How can you tell if your start-up is truly succeeding in its early stages? Revenue is the obvious metric – but it’s a lagging indicator. By the time sales numbers tell you something’s wrong, it’s often too late to fix. Instead, savvy CEOs watch the leading indicators – the forward-looking metrics that predict those sales. For example, if you know it takes 400 customer demos to hit your quarterly sales target, then the number of demos completed this month is a critical signal. Hitting that leading metric is an early green line sign that future revenue will follow. Falling short is a warning that you’re sliding into the red.

Early success in a start-up often shows up as momentum in these leading metrics. Maybe you’re seeing a surge in qualified leads, a growing pipeline of deals, or increasing product usage. Perhaps your customer retention is high – those who buy once keep coming back for more. Or you’re getting enthusiastic customer feedback and referrals (“We love it! I’ve told three other people about your product.”). These are the kind of early wins that matter. They’re the green shoots that predict a healthy harvest later.

Another underrated success indicator? Clarity and focus. Sounds abstract, but ask yourself: do you and your team know exactly who your core customer is and why they buy from you? Many start-ups don’t. If you’ve nailed a specific target customer and a compelling value proposition early on, that’s a huge green line indicator. It means your marketing and sales efforts can hit the mark. Clarity here tends to translate into easier wins and faster growth. Finally, team alignment and energy are subtle but important early signals. Is your team operating like a small, focused special forces unit, clear on the mission and executing with enthusiasm? Early chaos is normal in a start-up, but prolonged confusion is not.

Red flags already? Early warning signs you’re off-track

What does it look like when the wheels are wobbling early on? Lagging sales is the big obvious one. Maybe Q1 came in below target. Now April and May aren’t picking up the slack. But behind lagging sales, there are usually deeper issues. Think of low sales as the red flashing light on your dashboard. What’s causing it?

Often, the root causes of an off-track start-up show up in a few ways:

• Pipeline problems: You don’t have enough leads or opportunities to hit your future numbers. Maybe marketing leads are trickling in at a fraction of what you need, or your win rate is far lower than expected. If your pipeline isn’t bursting at the seams in early months, that’s a red line trending down. No pipeline = no sales next quarter, it’s that simple.
• Customer Apathy: Early customers aren’t engaging, using the product, or singing your praises. Perhaps your product usage is low or churn is creeping up. If new users sign up but go quiet, or initial clients aren’t renewing, alarm bells should be ringing. It’s a sign your value proposition isn’t landing, or you’ve attracted the wrong customers.
• Data Blindness: Here’s a scary one – you don’t actually have the data on the above points. I see this often: a scale-up client thinks things are fine, until we ask basic questions like “How many leads did you get this month? What’s your conversion rate?” and all we get are blank stares. If you’re not measuring the right things, you could be off-track and not even know it.

May: the make-or-break month

May is a brilliant time to course-correct. You have data from Q1 and early Q2. You have enough runway to implement changes and see results by year-end. You’re also past any early-year delusions that “maybe it’ll all magically work out.” By May, reality is staring you in the face with a quizzical look: “Well, what are you going to do about it?”

If you’re on or above target (your red and green lines overlap nicely), great – double down on what’s working. But if you’re behind, inaction is your enemy. The worst thing you can do now is cross your fingers and hope for a spontaneous recovery in Q3. Hope is not a strategy. Small problems compound into big ones. A slight miss in Q1 becomes a massive shortfall by Q4 if left unaddressed.

By summer, everyone’s either on holiday or frantically trying to close deals before the August lull. By autumn, the die is largely cast – enterprises lock in budgets, purchase decisions push to next year, and your team is either motivated by wins or demoralised by losses. May is your chance to intervene when there’s still time to influence Q3 and Q4 outcomes. Not convinced? Let’s put it in concrete terms: If sales are lagging now, to hit your annual number you either need higher velocity later (riskier and exhausting), or you change the game now. Wait until September and you simply won’t have enough runway for any changes to impact 2025’s numbers.

How to course-correct when sales are lagging

Alright, so you’ve realised you’re off-track. Sales are not where they should be. What now? Panicking and yelling at the sales team is one option, but let’s go with something more constructive. Here are some practical interventions to consider right now (not in three months, when you’re really in the soup):

• Revisit your pricing strategy: When was the last time you examined your prices? Too many start-ups set and forget their pricing, or price based on cost-plus thinking. Consider a value-based pricing approach. Can you raise prices (even modestly) for the value you’re delivering? Being bold on pricing now could boost your H2 revenue without needing a single extra customer. Don’t be afraid to be the most expensive option if you can justify it with superior value. And if your product’s value isn’t clear enough to support a higher price, that’s a strategy problem to fix pronto.
• Sharpen your go-to-market focus: If you’re chasing “anyone with a pulse and a wallet,” it’s time to stop. Go narrow and deep. Identify your ideal customer profile – the segment that gets massive value from your solution and will pay for it. Successful companies know precisely what they can be the best at and who will benefit most. Do you?
• Accelerate pipeline generation and management: If your leading indicators (like demos, trials, inbound leads) are low, turbocharge your pipeline. This could involve a short-term marketing blitz, reactivating old leads, or incentivising referrals from existing customers. Are you tracking those leading metrics weekly? Daily? If 400 demos a quarter is the goal, and you’re at 100 halfway through, you know you’re behind – so push your team to schedule more now, not in September. Have you set clear weekly KPIs for your sales team (calls made, proposals sent, demos completed)? What gets measured gets done. Make those numbers visible and unavoidable.
• Re-energise (or restructure) your team: Sometimes the issue isn’t what you’re selling or who you’re selling to, but who’s doing the selling. Take a hard look at your team. Do you have the right talent and accountability in place? Is your Head of Sales truly up to the task, or have they been “allowed to get away” with underperformance because no one confronted the data gap? It might be time for some tough conversations. If someone is clearly a poor fit for the journey ahead – well, as painful as it is, not acting is worse. One great hire can transform a business, and one poor hire can tank it, fast.
• Double down on your best customers: Not all customers are equal – a handful of them probably contribute a big chunk of your revenue. Can you upsell or cross-sell something to them? It’s far easier to get revenue from an existing happy customer than a cold prospect. But only do this ethically – it should genuinely help them, not just paper over your numbers. On the flip side, identify any customer segments that are draining resources for little return and consider pruning or deprioritising them (politely). It’s like gardening: water your roses, not your weeds. Focus resources where you get the best bloom.

Don’t wait for Q4 – course-correct now

By now, you should have a clear picture: early indicators of success are there if you look – and so are the early warning signs of trouble. A start-up doesn’t go from hero to zero overnight; the trajectory shift starts small. A missed target here, a slipping metric there. These are your red lines calling out for attention.The difference between a great year and an average one often comes down to when you act. May is a brilliant month for action. It’s late enough to have learned some lessons, and early enough to implement big changes. Whether it’s tweaking your pricing, refocusing your market, ramping up your pipeline, or even reshuffling your team, do it now. As the year progresses, your degrees of freedom decrease. By Q4, you’re mostly executing on decisions made months earlier. So make the right decisions today. After all, that green line won’t chase itself.

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Written by business coach and leadership coaching expert Dominic Monkhouse. Contact him to schedule a call here. You can order your free copy of his book, Mind Your F**king Business here.