In a changing legal market -- responding to a data-driven economy -- companies and law firms often play it safe, look for the perfect solution and wait for the right moment to jumpstart innovation of legal workflows. Investing into technology requires some expenses and the return on investment is often difficult to predict. Clearly, legal technology acquisitions need to be carefully and strategically considered. Yet study after study shows: strategic thinkers are found to be among the most highly effective leaders, and those organizations that look to the future and take well-managed risks are the ones that persevere and grow. We help apply this wisdom in legal innovation context.