Kris Duggan: Why Most Incentive Plans Fail (and How to Fix Them)


Startups often turn to bonuses and equity plans to drive motivation and performance, but these traditional approaches frequently fall short. Instead of creating alignment and engagement, they can lead to confusion, demotivation, and missed expectations. Many employees don’t understand how incentives are calculated, how their performance is measured, or how long‑term rewards like equity connect to their daily work.

Kris Duggan, a serial entrepreneur and a longtime advocate for transparent goal‑setting, put it simply: Very few employees today fully understand their company’s business strategies and what’s expected of them in order to help achieve company goals.” Duggan, a work-productivity expert who’s written on the issue for Entrepreneur and other publications, says consistency and clarity—more than compensation alone—is what drives productivity and engagement.

This is especially true in startups, Duggan says, where goals shift quickly, roles evolve constantly, and the pace of change outstrips legacy HR practices. Incentives built for corporate predictability often collapse under the dynamic conditions of early‑stage companies. Instead of motivating the right behaviors, they can unintentionally reward inertia, tenure, or even political maneuvering.

Why Traditional Bonus Models Backfire

One of the biggest issues with traditional bonuses is timing. Many companies distribute performance bonuses annually, long after the behavior they aim to reward. By the time the payout arrives, the connection between action and reward has faded. This delay reduces the motivational impact and leaves employees uncertain about what led to the bonus in the first place. What’s more, delayed feedback weakens the value of performance-based pay.

Another problem is how these bonuses are calculated. Employees are often unaware of the metrics or decision-making processes involved. Without transparency, bonuses feel arbitrary. This ambiguity breeds mistrust, especially when payouts vary widely without clear justification. When people can’t see how their actions translate into outcomes, they disengage from the process.

“Generic structures also fail to account for the specific needs of different roles,” notes Kris Duggan. “A bonus plan that works for a sales team might not apply to engineers or designers.” Yet companies frequently apply the same framework across departments, expecting similar results. These one-size-fits-all systems create frustration rather than motivation, especially for employees whose contributions are harder to quantify with revenue-based metrics.

Poorly designed bonuses can even backfire. In fact, offering a monetary attendance bonus increased absenteeism by around 45% among recently hired employees. The reward distorted behavior, as workers became more likely to manipulate the system or lose motivation once the bonus was introduced.

The Equity Illusion

Equity is often positioned as a long-term reward that aligns employees with the success of the company. While that theory has merit, its practical effectiveness is limited—especially in early-stage startups. Time-based vesting schedules prioritize tenure over contribution. An employee who stays for four years but delivers minimal impact is rewarded more than a short-term contributor who plays a key role in a product launch or revenue breakthrough.

Another issue is that equity value is frequently unclear or inaccessible. Private company stock doesn’t have a market value that employees can reference. Unless a company is close to an acquisition or IPO, equity feels more like a promise than a reward. Employees may not understand how many shares they have, what they’re worth, or when (if ever) they’ll be able to realize that value. Without clear communication, equity fails to serve as a motivational tool.

Startups also tend to overestimate the emotional weight of equity. Founders often assume that employees view stock options the same way they do—as ownership in something meaningful. But without ongoing context or education, most people don’t connect their day-to-day tasks to a distant liquidity event. When equity isn’t paired with other forms of recognition or feedback, it loses its intended impact.

Plus, equity-based rewards do little to reinforce short-term behaviors that drive momentum. Startups live and die by execution. Recognizing impact in the moment—rather than years later—is essential to maintaining focus and morale. Equity alone can’t provide that. It needs to be supplemented by incentives that reward immediate value creation and reinforce the pace and adaptability startups require.

What Actually Works: Performance-Based Rewards Done Right

Startups benefit most from incentives that focus on what employees can influence directly. Rather than rewarding lagging indicators like quarterly revenue, companies should tie bonuses and recognition to leading indicators—such as qualified leads generated, successful feature deployments, or customer satisfaction improvements. These metrics are more immediate and controllable, giving employees a clearer sense of how to win.

Regular and visible rewards create a much stronger connection between effort and recognition. Instead of waiting a full year to evaluate performance, managers can provide smaller bonuses or spot awards on a monthly or quarterly to reinforce desired behaviors and keep motivation levels high. It also provides managers with more opportunities to adjust targets or priorities in real-time.

Combining monetary rewards with non-monetary forms of recognition can further improve outcomes. According to a 2025 survey by Nectar, 77.9% of employees said they’d be more productive if they received recognition more frequently. Peer-nominated awards, executive shoutouts, or team celebrations contribute to a culture where good work doesn’t go unnoticed. These public acknowledgments carry weight, especially when they’re tied to specific achievements. Recognition doesn’t always have to cost money to be meaningful.

Ultimately, the most effective incentive plans are transparent, fair, and directly linked to business goals. Employees should know what they’re being measured against and how they can improve. Managers need tools and training to deliver feedback consistently. By focusing on clarity and timing, startups can build reward systems that not only motivate but also align teams around shared outcomes.

Final Takeaway

Most incentive plans don’t fail because companies are stingy. They fail because the design is disconnected from how people actually work and what motivates them in the moment. Bonuses and equity are only effective when employees understand them, believe in them, and see the results of their efforts reflected in them.

“For startups, the solution isn’t to spend more on compensation—it’s to spend smarter,” says Duggan. Incentives should be tailored to the rhythm of startup life: fast, iterative, and focused on outcomes. That means recognizing effort quickly, rewarding behaviors that lead to progress, and making expectations clear from the start.

Rethinking incentives also improves company culture. When people feel their contributions are seen and valued, they’re more likely to stay engaged and invested. That connection between recognition and belonging can’t be replaced by financial incentives alone, but the right system can reinforce it.

Startups that succeed in building better incentives will benefit from more than just improved performance metrics. They’ll build more trust, attract stronger talent, and create the conditions for sustained growth—not because their plans are flashy, but because they actually work.