You're navigating the complexities of IT Strategy. How can you effectively manage up with your boss?

When I built the IT Strategy for the first time, I collected the business strategy documents as the first step. The next step was to build a 3 year picture of To-Be scenario of major business processes in terms of business KPIs. The next step is to identify the business initiatives, and how IT has to support these initiatives. The resultant IT initiatives are either building capacity for business growth, or to build capabilities to support new business growth initiatives.

I am going to take a different perspective. As the CEO of the holding company over 2 companies in the IT, Telco and Emerging Technology categories, I desire input from my team relative to the deal pursuit(s). The pace of technology continues to accelerate which increases the gap in what I have known for years as well as the pros/cons of many emerging solutions. As an example, AI. Due in part to Nvidia stock gaining value at such a rapid pace on a Wednesday last summer, AI is plastered on just about all technologies. I want to ensure the AI enabled solutions our companies promote whether for Call Center efficiencies to generativeAI cloud overlays of existing IT point solutions, are tested as true/accurate outputs. Zero risk - wrong answers.

The core principle is IT strategy needs to align with the business strategy. Adopt below approach to manage IT strategy complexities with your boss: 1. Understand business strategy, roadmap, which are inputs to craft the IT strategy. 2. Discuss your boss’ priorities, align with IT initiatives. Agree what does success look like. 3. In addition, map your, your boss’ social styles. Asses how these styles interact in a working relationship. 4. Craft, communicate the plan to deliver the IT initiatives. 5. Be pro-active, periodically discuss with boss progress vs plan, challenges, risks, mitigation actions, course corrections. 6. This will enable to elicit guidance, support, build trust with your boss.

In order to manage the IT strategy, first of all, the company and senior management strategies must be determined. As IT, the first thing you do should be to put forward the projects and roadmap that are compatible with these strategies. By correctly determining your methods and metrics for measuring performance and success in your projects, you can ensure that your contributions are valued. Showing senior management the contribution and importance of your IT projects to these strategies will also provide you with more support.

The first step in managing up is to clearly understand your boss's goals and priorities. What are their key objectives in the IT strategy? What challenges are they facing? By aligning your work with their goals, you can ensure that your contributions are seen as valuable and relevant. Regularly ask for feedback to ensure you're on the right track and making a meaningful impact on the overall strategy.

When determining the IT strategy and roadmap, vague statements are the most challenging issues. The top challenges I had in creating an IT strategy were: - Lack of clarity in corporate strategies, - We tried to be as clear as possible when creating IT strategies, but there were differences in terminology and perspectives on projects with senior management. At this point, the solution is to convey to senior management in a language that they can understand, focusing on how IT projects and solutions can solve business problems or create opportunities. It is also important to express technical concepts that are complex in an understandable way.

Whats the purpose of strategy? The core purpose of strategy is communication. Communicating the multiple moving parts of your operations, investments and organisation strengthening in a coherent and connected manner. Building an IT Strategy gives you a coherent mindmap and communication tool to explain the grand plan to your boss. Not only to your boss, but to your own organisation as well as partners. Slice and dice your capability - capacity initiatives from different perspectives like organisational, partner and operational implications - to clarify your strategy.

Effective communication is essential in IT strategy, where complex technical details can easily get lost in translation. When discussing projects or updates with your boss, aim to be clear and concise. Avoid jargon and focus on the key points that are most relevant to your boss's interests. This not only helps in getting your message across but also demonstrates your ability to distill complex information into actionable insights.

Provide regular updates on your progress, especially on critical projects or initiatives. This keeps your boss informed and builds trust. Anticipate potential questions or concerns your boss might have and proactively address them in your communications. Finally, if you encounter challenges or potential roadblocks, communicate them early and offer potential solutions. This demonstrates initiative and problem-solving skills.

Don’t wait for your boss to ask for updates. Take the initiative to provide regular progress reports, highlighting any milestones achieved or potential roadblocks ahead. Being proactive shows that you are on top of your responsibilities and helps your boss stay informed without having to chase down information. This approach builds trust and ensures that there are no surprises down the line.

Don't just offer solutions but multiple alternatives you considered while approaching a solution. Every manager wants to help in taking decisions - that's a psychological need. So never take a single solution across. Bring alternatives with thought-through pros and cons to precede every decision with a healthy discussion. This will involve your boss in decision making and also build trust.

When challenges arise, it's important to present not just the problem but also potential solutions. Demonstrating problem-solving skills is a key aspect of managing up. Your boss will appreciate your initiative in finding ways to overcome obstacles, and it positions you as a reliable and resourceful team member. This also helps in fostering a collaborative relationship where you and your boss work together towards common goals.

Trust is a difficult concept to establish and very easy to destroy. It is also a key approach in managing not only top management but also all teams. Therefore, whether the company has corporate strategies or not, the first condition for establishing trust is to be consistent in the promises you make to achieve your IT strategies. For strategic projects, the scope of the work and therefore its quality will ensure that you reach your goals as much as the delivery date. In addition, establishing trust in strategy management shows that you are open to receiving feedback for projects as well as giving it and to working together.

Trust is also based upon telling your superiors when an IT solution has failed. When this happens, investigate/ask questions of the stakeholders to help identify the root cause of the failure, so if asked, your next-round solution can address that issue too.

"Trust takes years to build, seconds to break, and forever to repair" To build trust, one must be consistency in his/her deliveries, quality of deliveries and most important of all, his/her integrity. Without integrity, it is not possible for trust to be built and even if it is built, it is going to be fragile and will break easily.

Trust is the foundation of any effective working relationship. To build trust with your boss, consistently deliver on your promises, meet deadlines, and be transparent about any issues or delays. Trust is earned over time through reliability and integrity, and it plays a significant role in how your boss perceives your contributions to the IT strategy.

The IT landscape is constantly changing, and flexibility is key to managing up effectively. Be open to adjusting your approach based on feedback or shifts in strategy. Showing that you can adapt to new circumstances without losing focus on the end goal will make you a valuable asset to your boss and the organization.