What do you do if you're unsure of your boss's expectations and priorities in IT strategy?

If you don't know, Ask! - Speak with your boss and ask him what the organizational strategy is. - Find out what will make your boss successful! What are his/her specific goals that you can focus on? - Discuss what you are doing with your boss and determine if a change in direction is required - If your boss is open to transparent conversations and you feel that the strategy may require tweaking, have that conversation At the end of the day, work on making your boss successful, so that he/she will gain the influence to support your growth!

In IT strategy ambiguity, first step is to request a one-on-one with your boss. Use this meeting to ask straightforward questions about their vision and priorities. Listen intently, and then document the key points discussed for future reference. Regular check-ins are vital for staying aligned and adapting to evolving strategies. They show your dedication to meeting expectations and contributing effectively. Continuously educate yourself on emerging IT trends. This knowledge enables you to anticipate needs and propose solutions, potentially even before they're directly communicated. Being proactive and informed is crucial in the dynamic IT field.

While the Boss will always have a thought process around the IT strategy, when you go for a one on one meeting, it is always advisable to speak out your own thought process and arrive at a conclusion. It is imperative that when you create and present your point of view, it is based on the overall organisational objectives which are known to you. Once you have an initial alignment in this first meeting, create a point of view and get it validated with experts before you present it to a larger groups. External consultants are often handy in such endeavours

Check the then situation to find out what is needed by the enterprise. What are the KPIs for your Boss, do your omework to come up with a list what could help make your role a success for the enterprise and the boss. Request one on one with the boss. Share with boss that you want to discuss the expectations. If s/he would like you can share what you think else would like to hear from her/him. Listen well and summarise/rephrase for clarity.

And if you still don't understand, then better find another job. Either you are unsuited to this work,or your boss is either inarticulate, or thoroughly confused about the subject. Either way the project is doomed, so get out while you can!

Aligning IT initiatives with business goals is a strategic imperative. My advice is to not only review formal documents like mission statements and annual reports but also to engage in conversations with stakeholders across the business to gain a broader perspective. This holistic approach ensures that your IT strategy is not only aligned with documented goals but also resonates with the evolving needs and insights of the business, making your contributions both relevant and impactful.

Prepare Specific Questions before the meeting, that address your uncertainties. For example, ask about the key priorities for the IT department, how success is measured, and how your role specifically contributes (in details) to these objectives. Think also of a number of possible answers/ideas to those questions, to make the discussion smoother and productive.

IT Strategy fundamentally based on Company missions and visionary goals for next 3/4 years. To define IT strategy need to take past 1/2 years performance data along with annual reports, P&L and strategical KPIs achievements. During the strategy executions needs to aline with business goals achievements.

Collaboration extends beyond gathering insights; it's about building a shared vision for IT's role in the organization. I recommend creating regular touchpoints with peers to discuss ongoing and upcoming projects. Use these discussions to identify areas where your work can complement theirs, fostering a culture of collaboration. This not only helps you understand your boss's expectations but also encourages a team-oriented approach to achieving strategic IT objectives.

This can be a good thing as it gives you an opportunity to get to know the team. It will also help you find out what skills they have.

Your relationship with your boss is crucial in your work life. It can lead to economic satisfaction or, conversely, frustrations and even psychosomatic illnesses. Coming to a narrower point of view, the advice I have always received and given to my collaborators and colleagues is to create a serene, honest path of mutual respect. Unfortunately, my dear ones, we are human beings, and is, as we say in Italy, a “mere chimera” meaning an unattainable thing. All that remains is, as we say in Rome, to have two different attitudes: either comply with everything he asks of you, or encourage him to consider alternative perspectives that enhance different visions or your point of view. My experiences in this field with CEO or C-level are very bad.

Documentation is more than a record; it's a strategic tool. I've found that actively maintaining a "strategy log" – a dynamic document where you map out insights, decisions, and their rationales – can be incredibly valuable. This log serves as a living document that guides your strategic initiatives and provides a narrative of your strategic journey. It's a powerful way to demonstrate your strategic alignment and decision-making process to both your boss and your peers.

There is no size fits all. Change is a constant evolution to bring creative ideas and innovative solutions to adopt different variables in IT strategy to explore and exploit abundance

In my experience change starts small with a huge impact. Constant connect with you boss re-tearing what he said n rephrasing to your understanding will help you and your boss define the path for the IT strategy. This will also help you get a deep understanding of the need and align your team priorities & tasks. This will surely help you and your team to reach the final goal.

Pay attention to your boss's actions, decisions, and interactions with other team members to understand how they prioritize tasks and projects related to the IT strategy. This can help you anticipate their expectations and align your efforts accordingly.

In communication aspect, having cadence and accountability drives the clarity of the expectations and priorities because it will have changes and we adopt to it to achieve goals.

KPI should be coming from the respective stakeholders such as clients or business partners. Accountability is with the respective team to deliver. Needs to be clarified with the stakeholders and sponsors and should be documented and get signed off from all relevant parties as per the documented process.

All of the above points are very relevant. I believe if you understand the business plans of the company and what the company hope to achieve over the next few years you are in a better position to understand their IT strategies. This will give you a better understanding of what kind of IT systems will bring the company forward and make it more competitive. It will also demonstrate that you have leadership capability and that you are capable of understanding the big picture and your role in achieving the various goals set for the IT team.

Consider the broader organizational context in which these expectations are set. Understanding the company's overall strategic goals and how the IT strategy supports these can provide additional clarity. Additionally, fostering relationships with other team members and departments can offer insights into how your work fits into the larger organizational puzzle. By following these steps, you can more effectively understand and align with your boss’s expectations and priorities in IT strategy, contributing to the success of both your team and the broader organization.

To clarify your boss's expectations and priorities in IT strategy, take proactive steps such as scheduling a meeting to discuss key objectives, seeking feedback on your work performance, reviewing past communications for insights, observing your boss's actions to understand priorities, and collaborating with colleagues for guidance. Clear communication and proactive engagement are essential for aligning your efforts with your boss's goals and objectives.