Being a leader requires you to rise above your struggles and bring the team forward. Be it an external challenge such as lack of resources or even an internal dilemma in the form of getting into one’s head; the role of a leader challenges an individual to learn at the same time as imparting knowledge to the team.

Here are some challenges that one should be ready for when preparing for the responsibility of becoming a leader:


Part and parcel of leading a team or an entire organisation is the requirement of dealing with the external challenges. Some of which include lack of funding, opposition from forces in the community and even interpersonal problems within the team members.

Social, economic, and political forces in the larger world can affect the organization as well. To some extent, the measure of any leader is how well he can deal with the constant succession of crises and minor annoyances that threaten the team’s tasks and objectives. If they are able to make decisions to solve problems, take advantage of opportunities, and resolve conflicts.

If the leader doesn’t handle external challenges well, it will be reflected in the structure of the company as well as the morale of its team members. When people feel that leaders are stressed or unsure, they themselves adopt these behaviours, and the focus of the group moves from its mission to the current worrisome situation. The work of the group naturally suffers.

  1. Overemphasis on generational differences. Not that long ago leaders often seemed to ignore generational differences. The pendulum has swung to another extreme. There seems to be a belief that everyone is so different we can’t effectively lead!
    The New Savvy - Women - Leader
    Generations are different, and understanding those differences can provide effective tools for communication and opportunities to collaborate better. At the same time people regardless of age share much in common: the need to belong to a winning team, meaning in their work, satisfaction in the jobs they do, and much more. Leaders must balance understanding and use differences and unify their teams with shared interests and beliefs.
  2. Inspiring others is the challenge of inspiring or motivating others to ensure they’re satisfied with their jobs and working efficiently.
  3. Developing employees is the challenge of developing others, including mentoring and coaching.
  4. Guiding change is the challenge of managing, mobilizing, understanding, and leading change. Guiding change includes knowing how to mitigate consequences, overcome resistance to change, and deal with employees’ reactions to change.
  5. Managing internal stakeholders is the challenge of managing relationships, politics, and image. This challenge includes gaining managerial support, managing up, and getting buy-in from other departments, groups, or individuals.


Being a leader can expose us to many wondrous opportunities. The responsibility tests our ability to demonstrate the skills that made us worthy of the role in the first place.

It displays our strengths but it also exposes our weaknesses in the form of limitations. Overcoming fear, lack of confidence, insecurity and other psychological struggles can hinder an individual from becoming a great leader. 

It’s often very difficult for people, especially those who see themselves as leaders, to admit that they might have personality traits or personal characteristics that interfere with their ability to reach their goals. Part of good leadership is learning to accept the reality of those traits, and working to change them so they don’t get in the way.

  1.  Developing managerial effectiveness is the challenge of developing the relevant skills — such as time management, prioritization, strategic thinking, decision-making, and getting up to speed with the job — to be more effective at work.
  2. An increasing lack of confidence. Most leaders wouldn’t admit this (even when pressed), but they know that past success is no guarantee of future success and struggle with a crisis of confidence in their abilities to keep winning. Leaders sometimes fail. We act like that is a dirty secret. You work hard and do your best and that is all you can do. If you continue to succeed more than fail in your leadership role, that is proof you are in the right job. If your failure rate exceeds your win rate, that is important feedback that you might not be the right leader for the position.
  3. A false dichotomy of ethics. Trying to separate personal ethics from professional ethics is a bad idea. There are just ethics, and trying to apply two different standards isn’t just confusing, it is wrong. Why would you trust someone at work that you know to be a conniving liar in his or her personal life? And why would you allow something that you know is wrong to happen at work? One psychologist calls it the “normalization of deviance:” making it acceptable to do at work what is wrong to do outside work. Leaders work hard to create what I conversely call the “normalization of integrity.” Without clearly defined values that are lived and observed by others, ethics slip dangerously.
  4. Employee engagement. It is as important as competing for talent, a common dilemma according to my clients. One of the biggest myths I encounter is the belief that if you just get the best people on your team, your job is done. John Wooden wisely noted that he didn’t want the best players on his team. He wanted the players that made his team best. That points to the importance of engagement and teamwork. Talent alone is a start, but it is never enough. Divisive star players and disengaged genius are both liabilities. Good leaders find the best people and then focus on keeping those they’ve found engaged.
  5. Lack of preparation to successfully lead. Research shows that only one in four leaders feels prepared when they assume formal leadership positions. Leaders need to learn to lead before they obtain the formal opportunity, not after. And that isn’t accomplished just through books and courses but through real-world projects and assignments where leadership skills are developed. If you don’t give your team members a chance to lead before they become formal leaders, they will lack the skills and confidence to lead when they move into management.






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Founder @ The New Savvy
Anna Haotanto is the Advisor (former CEO) of The New Savvy. She is currently the COO of ABZD Capital and the CMO of Gourmet Food Holdings, an investment firm focusing on opportunities in the global F&B industry. She is part of the founding committee of the Singapore FinTech Association and heads the Women In FinTech and Partnership Committee. Anna is the President of the Singapore Management University Women Alumni. Anna invests and sits on the board of a few startups. Anna is also part of the Singapore Chinese Chamber of Commerce & Industry Career Women’s Group executive committee. Anna’s story is featured on Millionaire Minds on Channel NewsAsia. She hosts TV shows and events, namely for Channel NewsAsia’s “The Millennial Investor” and “Challenge Tomorrow”, a FinTech documentary. Anna was awarded “Her Times Youth Award” at the Rising50 Women Empowerment Gala, organised by the Indonesian Embassy of Singapore. The award was presented by His Excellency Ngurah Swajaya. She was also awarded Founder of the Year for ASEAN Rice Bowl Startup Awards. She was also awarded the Women Empowerment Award by the Asian Business & Social Forum. Anna has been awarded LinkedIn Power Profiles for founders (2018, 2017), Tatler Gen T, The Peak’s Trailblazers under 40 and a nominee for the Women of The Future award by Aviva


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