Can you recall a time in your career when you made a mistake? I certainly can, and many at that. Inevitably, if you are playing it safe, you will always win, but if you are up to big things, you will unquestionably experience painful but important failures. It's my view that the mistake or failure itself is far less important than how that event inspired and shaped your thinking going forward.

Eswar Priyadarshan, serial founder who sold his three technology businesses for a combined value of $575 Million, once held a position where he reported directly to Steve Jobs after Apple bought his second company, Quattro Wireless. As a guest on the Unmessable show, he recalled a specific leadership mistake Jobs made that taught him an invaluable lesson.

Quattro, then a leading global mobile advertising company that helped advertisers to reach and engage their target audiences, was acquired in March of 2010 to power Apple's mobile advertising platform called Apple iAd.

At the time, Priyadarshan, under Jobs' leadership, was told that advertisers would pay whatever Apple demanded, because...well, they were Apple.

But Jobs was wrong, Priyadarshan said. His success had blinded him to an imminent market change. The advertising landscape increasingly demanded more rigorous tracking of ad performance to assess return on investment, particularly as Google's AdWords business' grew. Priyadarshan, and his team, intuitively knew Jobs' approach was wrong, but given the track record of their boss, they conceded.

Eventually, this decision led to Apple's iAd platform shut down in 2016. Apple's dominant tech power, which Jobs had created and had come to rely upon, was not sufficient to overcome the tight ad spending grip of the ad agencies. Hindsight, Priyadarshan now knows that regardless of who is in the leadership position and what their track record is, he will always listen to his instincts.

When you are at the top of your game, leading a growing company, you are less likely to notice major market changes as they are unfolding, and that's where Jobs failed. No matter how successful you are as a company or a leader, you have to be on alert to anticipate market shifts and adapt your business accordingly.

So, what are some ways you can positively anticipate a market shift before the turning point occurs? Priyadarshan outlines the five strategies he uses to diagnose an imminent market shift looming:


Complacency will create blind spots -- avoid this.

Once you've reached a certain level of success, it can be easy to fall into the trap of complacency. Priyadarshan says Jobs should have seen the change coming, particularly because of his relationship with Eric Schmidt, who was leading Google at the time. 

You must be hyper--alert to anything that has the potential to threaten the success you've built, whether that be a shift in market trends or an influx of new competitors.

Your sales staff will notice a market change first.

Significant market changes don't happen overnight. Often there will be clear indicators that demand for your product or service has declined, and it's your responsibility to take notice before a small problem turns into a big one.

For instance, a colder reception from customers will be felt first by your sales team Priyadarshan says, so be sure to implement clear feedback lines going back to top leadership in a strategic manner.

Always be on the lookout for superior technologies or rising competitors.

If it seems like there is always a new technology on the market, that's because there probably is. You can't afford to neglect these.

Make it a point to be hyper-aware of what else is out there. Set aside a small part of your day to digest the latest information surrounding your industry, Priyadarshan recommends. Even just keeping up with social media and what other industry leaders are saying can keep you in-the-know.

Engage key staff to help identify potential inflection points.

The typical reaction of most CEOs, when confronted with early signs of a market shift, is denial-- like Jobs. If you feel yourself doing that, stop. Discuss with your key team members the potential market shift. While it's a CEO's job to be the key decision maker in times of trouble, the input of others is crucial to finding a viable solution.

Strategically plan for the market shift.

Tough decisions will be required and may cause chaos for a period, but it will be necessary to adjust to change. Whether your plan includes experimenting with new strategies, diversifying your income, or working with different partners, it will take a team effort to approach and weather the storm of big changes, and you'll need your entire team onboard to make it happen efficiently.